3-aryl-4-hydroxy-Δ3 -dihydrofuranone derivatives

ABSTRACT

The present invention relates to a new 3-aryl-4-hydroxy-Δ 3  -dihydrofuranone derivatives of the general formula (I) ##STR1## in which the radicals A, B, G, X, Y, Z and n have the meaning given in the description, to a plurality of processes for their preparation, and to their use as pesticides.

This application is a divisional of application Ser. No. 08/303,987,filed Sep. 9, 1994 now U.S. Pat. No. 5,610,122.

The present invention relates to new 3-aryl-4-hydroxy-Δ³-dihydrofuranone derivatives, to processes for their preparation and totheir use as pesticides.

It has been disclosed that certain substituted Δ³ -di-hydrofuran-2-onederivatives have herbicidal properties (cf. DE-A 4,014,420). DE-A4,014,420 also describes the synthesis of the tetronic acid derivativesused as starting compounds (such as, for example,3-(2-methylphenyl)-4-hydroxy-5-(4-fluorophenyl)-Δ³ -dihydrofuran-2-one).Compounds which have a similar structure are known from the publicationCampbell et al., J. Chem. Soc., Perkin Trans. 1 1985, (8) 1567-76, butno insecticidal and/or acaricidal activity is indicated. Furthermore, EP528,156 discloses 3-aryl-Δ³ -dihydrofuranone derivatives havingherbicidal, acaricidal and insecticidal properties, but the activitydescribed therein is not always sufficient.

New 3-aryl-4-hydroxy-Δ³ -dihydrofuranone derivatives of the formula (I)##STR2## in which X represents alkyl, halogen, alkoxy or halogenoalkyl,

Y represents hydrogen, alkyl, halogen, alkoxy or halogenoalkyl,

Z represents alkyl, halogen or alkoxy,

n represents a number from 0-3,

or in which the radicals X and Z together with the phenyl radical towhich they are bonded form the naphthalene radical of the formula##STR3## in which Y has the abovementioned meaning, G representshydrogen (a) or the groups ##STR4## A and B together with the carbonatom to which they are bonded form a cycle which is substituted byalkoxy, alkylthio, alkylsulphoxyl, alkylsulphonyl, carboxyl or 2 or CO₂R² or

A and B together with the carbon atom to which they are bonded representa cycle in which two substituents together with the carbon atoms towhich they are bonded represent a saturated cycle which is optionallysubstituted by alkyl, alkoxy or halogen and which can be interrupted byoxygen or sulphur,

E.sup.⊕ represents a metal ion equivalent or an ammonium ion,

L and M represent in each case oxygen or sulphur,

R¹ represents in each case optionally substituted alkyl, alkenyl,alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl or cycloalkyl which can beinterrupted by at least one hetero atom, in each case optionallysubstituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl orhetaryloxyalkyl and

R² represents alkyl, cycloalkyl, alkenyl, alkoxyalkyl orpolyalkoxyalkyl, each of which is optionally substituted or representsin each case optionally substituted phenyl or benzyl,

R³, R⁴ and R⁵ independently of one another represent alkyl, alkoxy,alkylamino, dialkylamino, alkylthio, alkenylthio, alkinylthio orcycloalkylthio, each of which is optionally substituted by halogen, andin each case optionally substituted phenyl, phenoxy or phenylthio,

R⁶ and R⁷ independently of one another represent hydrogen, or representalkyl, alkenyl, alkoxy or alkoxyalkyl, each of which is optionallysubstituted by halogen, optionally substituted phenyl, optionallysubstituted benzyl,

or in which R⁶ and R⁷ together represent an alkylene radical which isoptionally interrupted by oxygen or sulphur, and the stereomerically andenantiomerically pure forms of compounds of the formula (1) have nowbeen found.

Taking into account the various meanings (a), (b), (c), (d), (e), (f)and (g) of Group G of the general formula (I), the following mainstructures (Ia) to (Ig) result: ##STR5## in which A, B, E, L, M, X, Y,Z, R¹, R², R³, R⁴, R⁵, R⁶, R⁷ and n have the abovementioned meanings.

Furthermore, it has been found that 3-aryl-4-hydroxy-Δ³ -dihydrofuranonederivatives of the formula (Ia) ##STR6## in which A, B, X, Y, Z and nhave the abovementioned meaning,

are obtained when

(A) carboxylic esters of the formula (II) ##STR7## in which A, B, X, Y,Z and n have the abovementioned meaning and

R⁸ represents alkyl,

are subjected to an intramolecular condensation reaction in the presenceof a diluent and in the presence of a base.

(B) Furthermore, it has been found that compounds of the formula (Ib)##STR8## in which A, B, X, Z, R¹ and n have the abovementioned meaning,are obtained when compounds of the formula (Ia) ##STR9## in which A, B,X, Y, Z and n have the abovementioned meaning,

α) are reacted with acid halides of the general formula (III) ##STR10##in which R¹ has the abovementioned meaning and

Hal represents halogen, in particular chlorine or bromine,

if appropriate in the presence of a diluent, and if appropriate in thepresence of an acid-binding agent,

or

β) are reacted with carboxylic anhydrides of the general formula (IV)

    R.sup.1 --CO--O--CO--R.sup.1                               (IV)

in which

R¹ has the abovementioned meaning, if appropriate in the presence of adiluent and if appropriate in the presence of an acid-binding agent.

(C) Furthermore, it has been found that compounds of the formula (Ic)##STR11## in which A, B, X, Y, Z, R² and n have the abovementionedmeaning,

L represents oxygen and

M represents oxygen or sulphur, are obtained when compounds of theformula (Ia) ##STR12## in which A, B, X, Y, Z and n have theabovementioned meaning,

are reacted with chloroformic esters or chloroformic thioesters of thegeneral formula (V)

    R.sup.2 --M--CO--Cl                                        (V)

in which

R² and M have the abovementioned meaning,

if appropriate in the presence of a diluent and if appropriate in thepresence of an acid-binding agent.

(D) Furthermore, it has been found that compounds of the formula (Ic)##STR13## in which A, B, R², X, Y, Z and n have the abovementionedmeaning,

L represents sulphur and

M represents oxygen or sulphur, are obtained when compounds of theformula (Ia) ##STR14## in which A, B, X, Y, Z and n have theabovementioned meaning

are reacted with chloromonothioformic esters or chlorodithioformicesters of the general formula (VI) ##STR15## in which M and R² have theabovementioned meaning,

if appropriate in the presence of a diluent and if appropriate in thepresence of an acid-binding agent.

(E) Furthermore, it has been found that compounds of the formula (Id)##STR16## in which A, B, X, Y, Z, R³ and n have the abovementionedmeaning, are obtained when compounds of the formula (Ia) ##STR17## inwhich A, B, X, Y, Z and n have the abovementioned meaning,

are reacted with sulphonyl chlorides of the general formula (VII)

    R.sup.3 --SO.sub.2 --Cl                                    (VII)

in which

R³ has the abovementioned meaning,

if appropriate in the presence of a diluent and if appropriate in thepresence of an acid-binding agent.

(F) Furthermore, it has been found that compounds of the formula (Ie)##STR18## in which A, B, L, X, Y, Z, R⁴, R⁵ and n have theabovementioned meaning,

are obtained when compounds of the formula (Ia) ##STR19## in which A, B,X, Y, Z and n have the abovementioned meaning

are reacted with phosphorus compounds of the general formula (IX)##STR20## in which L, R⁴ and R⁵ have the abovementioned meaning and

Hal represents halogen, in particular chlorine or bromine,

if appropriate in the presence of a diluent and if appropriate in thepresence of an acid-binding agent.

(G) Furthermore, it has been found that compounds of the formula (If)##STR21## in which A, B, L, X, Y, Z, R⁶, R⁷ and n have theabovementioned meaning,

are obtained when compounds of the formula (Ia) ##STR22## in which A, B,X, Y, Z and n have the abovementioned meaning

α) are reacted with isocyanates of the general formula (IX)

    R.sup.6 --N═C═L                                    (IX)

in which

L and R⁶ have the abovementioned meaning,

if appropriate in the presence of a diluent and if appropriate in thepresence of a catalyst,

or

β) are reacted with carbamoyl chlorides or thiocarbamoyl chlorides ofthe general formula (X) ##STR23## in which L, R⁶ and R⁷ have theabovementioned meaning,

if appropriate in the presence of a diluent and if appropriate in thepresence of an acid-binding agent.

H) Furthermore, it has been found that compounds of the formula (Ig)##STR24## in which X, Y, Z, A, B and n have the abovementioned meaning,

and E.sup.⊕ represents a metal ion equivalent or an ammonium ion,

are obtained when compounds of the formula (Ia) ##STR25## in which X, Y,Z, A, B and n have the abovementioned meaning,

are reacted with metal compounds or amines of the general formulae (XI)and (XII) ##STR26## in which Me represents mono- or divalent metal ions,

t represents the number 1 or 2,

R⁹ represents hydrogen, hydroxy or alkoxy and

R¹⁰, R¹¹ and R¹² independently of one another represent hydrogen oralkyl, if appropriate in the presence of a diluent.

Furthermore, it has been found that the new 3-aryl-4-hydroxy-Δ³-dihydrofuranone derivatives of the formula (I) are distinguished byoutstanding acaricidal, insecticidal and herbicidal activities, whichmakes them suitable for use as pesticides.

Preferred compounds of the formula (I) are those

in which

X represents C₁ -C₆ -alkyl, halogen, C₁ -C₆ -alkoxy or C₁ -C₃-halogenoalkyl,

Y represents hydrogen, C₁ -C₆ -alkyl, halogen, C₁ -C₆ -alkoxy or C₁ -C₃-halogenoalkyl,

Z represents C₁ -C₆ -alkyl, halogen or C₁ -C₆ -alkoxy,

n represents a number from 0 to 3,

or in which the radicals X and Z together with the phenyl radical towhich they are bonded form the naphthalene radical of the formula##STR27## in which Y has the abovementioned meaning, or in which

A and B together with the carbon atom to which they are bonded form asaturated or unsaturated 3- to 8-membered ring which is substituted byC₁ -C₆ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphoxyl or C₁ -C₄-alkylsulphonyl, carboxyl or C₂ R² or

A and B together with the carbon atom to which they are bonded representa C₃ -C₈ -membered ring in which two substituents together with thecarbon atoms to which they are bonded represent a saturated C₅ -C₇ -ringwhich is optionally substituted by C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy orhalogen and which can be interrupted by oxygen or sulphur,

G represents hydrogen (a) or the groups ##STR28## in which E.sup.⊕represents a metal ion equivalent or an ammonium ion,

L and M in each case represent oxygen or sulphur,

R¹ represents in each case optionally halogen-substituted C₁ -C₂₀-alkyl, C₂ -C₂₀ -alkenyl, C₁ -C₈ -alkoxy-C₁ -C₈ -alkyl, C₁ -C₈-alkylthio-C₁ -C₈ -alkyl, C₁ -C₈ -polyalkoxy-C₁ -C₈ -alkyl or C₃ -C₈-cycloalkyl, which is optionally substituted by halogen or C₁ -C₆ -alkyland which can be interrupted by at least one oxygen and/or sulphur atom,

phenyl which is optionally substituted by halogen, nitro, C₁ -C₆ -alkyl,C₁ -C₆ -alkoxy, C₁ -C₆ -halogenoalkyl or C₁ -C₆ -halogenoalkoxy,

phenyl-C₁ -C₆ -alkyl which is optionally substituted by halogen, C₁ -C₆-alkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -halogenoalkyl or C₁ -C₆ -halogenoalkoxy,

hetaryl which is optionally substituted by halogen and/or C₁ -C₆ -alkyl,

phenoxy-C₁ -C₆ -alkyl which is optionally substituted by halogen and/orC₁ -C₆ -alkyl,

hetaryloxy-C₁ -C₆ -alkyl which is optionally substituted by halogen,amino and/or C₁ -C₆ -alkyl,

R² represents C₁ -C₂₀ -alkyl, C₃ -C₂₀ -alkenyl, C₁ -C₈ -alkoxy-C₂ -C₈-alkyl or C₁ -C₈ -polyalkoxy-C₂ -C₈ -alkyl,

each of which is optionally substituted by halogen,

C₃ -C₈ -cycloalkyl, which is optionally substituted by halogen or C₁ -C₆-alkyl,

phenyl or benzyl, each of which is optionally substituted by halogen,nitro, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy or C₁ -C₆ -halogenoalkyl,

R³, R⁴ and R⁵ independently of one another represent C₁ -C₈ -alkyl, C₁-C₈ -alkoxy, C₁ -C₈ -alkylamino, di-(C₁ -C₈)-alkylamino, C₁ -C₈-alkylthio, C₂ -C₅ -alkenylthio, C₂ -C₅ -alkinylthio or C₃ -C₇-cycloalkylthio, each of which is optionally substituted by halogen, orrepresent phenyl, phenoxy or phenylthio, each of which is optionallysubstituted by halogen, nitro, cyano, C₁ -C₄ -alkoxy, C₁ -C₄-halogenoalkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -halogenoalkylthio, C₁ -C₄-alkyl or C₁ -C₄ -halogenoalkyl,

R⁶ and R⁷ independently of one another represent hydrogen or representC₁ -C₂₀ -alkyl, C₁ -C₂₀ -alkoxy, C₃ -C₈ -alkenyl or C₁ -C₂₀ -alkoxy-C₁-C₂₀ -alkyl, each of which is optionally substituted by halogen, phenylwhich is optionally substituted by halogen, C₁ -C₂₀ -halogenoalkyl, C₁-C₂₀ -alkyl or C₁ -C₂₀ -alkoxy, benzyl which is optionally substitutedby halogen, C₁ -C₂₀ -alkyl, C₁ -C₂₀ -halogenoalkyl or C₁ -C₂₀ -alkoxy,or together represent a C₄ -C₆ -alkylene ring which is optionallyinterrupted by oxygen or sulphur,

and the stereomerically and enantiomerically pure forms of compounds ofthe formula (I).

Particularly preferred compounds of the formula (I) are those in which

X represents C₁ -C₆ -alkyl, halogen, C₁ -C₆ -alkoxy or C₁ -C₆-halogenoalkyl,

Y represents hydrogen, C₁ -C₆ -alkyl, halogen, C₁ -C₆ -alkoxy or C₁ -C₂-halogenoalkyl,

Z represents C₁ -C₄ -alkyl, halogen or C₁ -C₄ -alkoxy,

n represents a number from 0 to 2,

or in which the radicals X and Z together with the phenyl radical towhich they are bonded form the naphthalene radical of the formula##STR29## in which Y has the abovementioned meaning, A and B togetherwith the carbon atom to which they are bonded form saturated orunsaturated, 5- to 7-membered ring which is substituted by C₁ -C₅-alkoxy, C₁ -C₃ -alkylthio, C₁ -C₃ -alkylsulphoxyl or C₁ -C₃-alkylsulphonyl, carboxyl or CO₂ R² or

A and B together with the carbon atom to which they are bonded representa C₄ -C₇ -membered ring in which two substituents together with thecarbon atoms to which they are bonded represent a saturated C₅ -C₆ -ringwhich is optionally substituted by C₁ -C₃ -alkyl, C₁ -C₃ -alkoxy,fluorine or chlorine and which can be interrupted by oxygen or sulphur,

G represents hydrogen (a) or the groups ##STR30## in which E.sup.⊕represents a metal ion equivalent or an ammonium ion,

L and M in each case represent oxygen or sulphur,

R¹ represents in each case optionally halogen-substituted C₁ -C₁₆-alkyl, C₂ -C₁₆ -alkenyl, C₁ -C₆ -alkoxy-C₁ -C₆ -alkyl, C₁ -C₆-alkylthio-C₁ -C₆ -alkyl, C₁ -C₆ -polyalkoxy-C₁ -C₆ -alkyl or C₃ -C₇-cycloalkyl, which is optionally substituted by chlorine or C₁ -C₄-alkyl and which can be interrupted by 1-2 oxygen and/or sulphur atoms,

phenyl which is optionally substituted by halogen, nitro, C₁ -C₄ -alkyl,C₁ -C₄ -alkoxy, C₁ -C₃ -halogenoalkyl or C₁ -C₃ -halogenoalkoxy,

or represents phenyl-C₁ -C₄ -alkyl which is optionally substituted byhalogen, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₃ -halogenoalkyl, or C₁ -C₃-halogenoalkoxy,

or represents furanyl, thienyl, pyridyl, pyrimidyl, thiazolyl orpyrazolyl each of which is optionally substituted by halogen and/or C₁-C₆ -alkyl,

phenoxy-C₁ -C₅ -alkyl which is optionally substituted by halogen and/orC₁ -C₄ -alkyl,

pyridyloxy-C₁ -C₅ -alkyl, pyrimidyloxy-C₁ -C₅ -alkyl or thiazolyloxy-C₁-C₅ -alkyl, each of which is optionally substituted by halogen, aminoand/or C₁ -C₄ -alkyl,

R² represents in each case optionally halogen-substituted C₁ -C₆ -alkyl,C₃ -C₆ -alkenyl, C₁ -C₆ -alkoxy-C₂ -C₆ -alkyl or C₁ -C₆ -polyalkoxy-C₂-C₆ -alkyl,

or represents C₃ -C₇ -cycloalkyl, which is optionally substituted byfluorine, chlorine or C₁ -C₄ -alkyl,

phenyl or benzyl, each of which is optionally substituted by halogen,nitro, C₁ -C₄ -alkyl, C₁ -C₃ -alkoxy or C₁ -C₃ -halogenoalkyl,

R³, R⁴ and R⁵ independently of one another represent C₁ -C₆ -alkyl, C₁-C₆ -alkoxy, C₁ -C₆ -alkylamino, di-(C₁ -C₆)-alkylamino, C₁ -C₆-alkylthio, C₃ -C₄ -alkenylthio, C₂ -C₄ -alkinylthio or C₃ -C₆-cycloalkylthio, each of which is optionally substituted by halogen, orrepresent phenyl, phenoxy or phenylthio, each of which is optionallysubstituted by fluorine, chlorine, bromine, nitro, cyano, C₁ -C₃-alkoxy, C₁ -C₃ -halogenoalkoxy, C₁ -C₃ -alkylthio, C₁ -C₃-halogenoalkylthio, C₁ -C₃ alkyl or C₁ -C₃ -halogenoalkyl,

R⁶ and R⁷ independently of one another represent hydrogen or representC₁ -C₂₀ -alkyl, C₁ -C₂₀ -alkoxy, C₃ -C₈ -alkenyl or C₁ -C₂₀ -alkoxy-C₁-C₂₀ -alkyl, each of which is optionally substituted by halogen, orrepresent phenyl which is optionally substituted by halogen, C₁ -C₅halogenoalkyl, C₁ -C₅ alkyl or C₁ -C₅ alkoxy, or represent benzyl whichis optionally substituted by halogen, C₁ -C₅ -alkyl, C₁ -C₅-halogenoalkyl or C₁ -C₅ -alkoxy, or together represent a C₄ -C₆-alkylene ring which is optionally interrupted by oxygen or sulphur,

and the stereomerically and enantiomerically pure forms of compounds offormula (I).

Very particularly preferred compounds of the formula (I) are those inwhich

X represents methyl, ethyl, propyl, i-propyl, fluorine, chlorine,bromine, methoxy, ethoxy or trifluoromethyl,

Y represents hydrogen, methyl, ethyl, propyl, i-propyl, butyl, i-butyl,tert-butyl, fluorine, chlorine, bromine, methoxy, ethoxy ortrifluoromethyl,

Z represents methyl, ethyl, i-propyl, butyl, i-butyl, tert-butyl,fluorine, chlorine, bromine, methoxy or ethoxy,

n represents 0 or 1,

A and B together with the carbon atom to which they are bonded form asaturated or unsaturated 5- to 6-membered ring which is substituted byC₁ -C₄ -alkoxy, C₁ -C₂ -alkylthio, C₁ -C₂ -alkylsulphoxyl or C₁ -C₂-alkylsulphonyl, carboxyl or CO₂ R² or

A and B together with the carbon atom to which they are bonded representa C₄ -C₆ -membered ring in which two substituents together with thecarbon atoms to which they are bonded represent a saturated C₅ -C₆ -ringwhich is optionally substituted by methyl, ethyl, methoxy, ethoxy,fluorine or chlorine and which can be interrupted by oxygen or sulphur,

G represents hydrogen (a) or the groups ##STR31## in which E.sup.⊕represents a metal ion equivalent or an ammonium ion,

L and M in each case represent oxygen or sulphur,

R¹ represents in each case optionally fluorine- or chlorine-substitutedC₁ -C₁₄ -alkyl, C₂ -C₁₄ -alkenyl, C₁ -C₄ -alkoxy-C₁ -C₆ -alkyl, C₁ -C₄-alkylthio-C₁ -C₆ -alkyl, C₁ -C₄ -polyalkoxy-C₁ -C₄ -alkyl or C₃ -C₆-cycloalkyl, which is optionally substituted by fluorine, chlorine,methyl or ethyl and which can be interrupted by 1-2 oxygen and/orsulphur atoms, or represents phenyl which is optionally substituted byfluorine, chlorine, bromine, methyl, ethyl, propyl, i-propyl, methoxy,ethoxy, trifluoromethyl, trifluoromethoxy or nitro,

or represents phenyl-C₁ -C₃ -alkyl which is optionally substituted byfluorine, chlorine, bromine, methyl, ethyl, propyl, i-propyl, methoxy,ethoxy, trifluoromethyl or trifluoromethoxy,

or represents furanyl, thienyl, pyridyl, pyrimidyl, thiazolyl orpyrazolyl, each of which is optionally substituted by fluorine,chlorine, bromine, methyl or ethyl,

or represents phenoxy-C₁ -C₄ -alkyl which is optionally substituted byfluorine, chlorine, methyl or ethyl,

or represents pyridyloxy-C₁ -C₄ -alkyl, pyrimidyloxy-C₁ -C₄ -alkyl orthiazolyloxy-C₁ -C₄ -alkyl, each of which is optionally substituted byfluorine, chlorine, amino, methyl or ethyl,

R² represents C₁ -C₁₄ -alkyl, C₃ -C₁₄ -alkenyl, C₁ -C₄ -alkoxy-C₂ -C₆-alkyl or C₁ -C₄ -polyalkoxy-C₂ -C₆ -alkyl, each of which is optionallysubstituted by fluorine or chlorine,

or represents C₃ -C₆ -cycloalkyl, which is optionally substituted byfluorine, chlorine, methyl or ethyl,

or represents phenyl or benzyl, each of which is optionally substitutedby fluorine, chlorine, nitro, methyl, ethyl, propyl, i-propyl, methoxy,ethoxy or trifluoromethyl,

R³, R⁴ and R⁵ independently of one another represent C₁ -C₄ -alkyl, C₁-C₄ -alkoxy, C₁ -C₄ -alkylamino, di-(C₁ -C₄ -alkyl)amino or C₁ -C₄-alkylthio, each of which is optionally substituted by fluorine orchlorine, or represents phenyl, phenoxy or phenylthio, each of which isoptionally substituted by fluorine, chlorine, bromine, nitro, cyano, C₁-C₂ -alkoxy, C₁ -C₄ -fluoroalkoxy, C₁ -C₂ -chloroalkoxy, C₁ -C₂-alkylthio, C₁ -C₂ -fluoroalkylthio, C₁ -C₂ -chloroalkylthio or C₁ -C₃-alkyl,

R⁶ and R⁷ independently of one another represent hydrogen or representC₁ -C₁₀ -alkyl, C₃ -C₆ -alkenyl, C₁ -C₁₀ alkoxy or C₁ -C₁₀ -alkoxy-C₁-C₁₀ -alkyl, each of which is optionally substituted by fluorine,chlorine or bromine, or represent phenyl which is optionally substitutedby fluorine, chlorine, bromine, C₁ -C₂ -halogenoalkyl, C₁ -C₂ -alkyl orC₁ -C₄ -alkoxy, or represent benzyl which is optionally substituted byfluorine, chlorine, bromine, C₁ -C₄ -alkyl, C₁ -C₄ -halogenoalkyl or C₁-C₄ -alkoxy, or together represent a C₄ -C₆ -alkylene ring which isoptionally interrupted by oxygen or sulphur,

and the stereomerically and enantiomerically pure forms of compounds ofthe formula (I).

The following 3-aryl-4-hydroxy-Δ³ -dihydrofuranone derivatives of theformula (Ia) may be mentioned individually in addition to the compoundsmentioned in the preparation examples:

                  TABLE 1                                                         ______________________________________                                         ##STR32##                                                                    X     Y       Z.sub.n  A    B                                                 ______________________________________                                        Cl    Cl      H        (CH.sub.2).sub.4CH(OCH.sub.3)                          Cl    Cl      H        (CH.sub.2).sub.3CH(OCH.sub.3)CH.sub.2                  Cl    Cl      H        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2          Cl    Cl      H        (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.                           2                                                      Cl    Cl      H        (CH.sub.2).sub.2CH(OC.sub.3 H.sub.7)(CH.sub.2).sub.                           2                                                      Cl    Cl      H        (CH.sub.2).sub.2CH(O-i-C.sub.3 H.sub.7)(CH.sub.2).s                           ub.2                                                   Cl    Cl      H        (CH.sub.2).sub.2CH(O-t-C.sub.4 H.sub.9)(CH.sub.2).s                           ub.2                                                   Cl    Cl      H        (CH.sub.2).sub.3CH(SCH.sub.3)CH.sub.2                  Cl    Cl      H        (CH.sub.2).sub.2CH(SCH.sub.3)(CH.sub.2).sub.2          Cl    Cl      H                                                                                       ##STR33##                                             Cl    Cl      H                                                                                       ##STR34##                                             Cl    Cl      H                                                                                       ##STR35##                                             Cl    Cl      H                                                                                       ##STR36##                                             Cl    Cl      H                                                                                       ##STR37##                                             Cl    Cl      H                                                                                       ##STR38##                                             Cl    Cl      H                                                                                       ##STR39##                                             Cl    Cl      H                                                                                       ##STR40##                                             CH.sub.3                                                                            CH.sub.3                                                                              H        (CH.sub.2).sub.4CH(OCH.sub.3)                          CH.sub.3                                                                            CH.sub.3                                                                              H        (CH.sub.2).sub.3CH(OCH.sub.3)CH.sub.2                  CH.sub.3                                                                            CH.sub.3                                                                              H        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2          CH.sub.3                                                                            CH.sub.3                                                                              H        (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.                           2                                                      CH.sub.3                                                                            CH.sub.3                                                                              H        (CH.sub.2).sub.2CH(OC.sub.3 H.sub.7)(CH.sub.2).sub.                           2                                                      CH.sub.3                                                                            CH.sub.3                                                                              H        (CH.sub.2).sub.2CH(O-i-C.sub.3 H.sub.7)(CH.sub.2).s                           ub.2                                                   CH.sub.3                                                                            CH.sub.3                                                                              H        (CH.sub.2).sub.2CH(O-t-C.sub.4 H.sub.9)(CH.sub.2).s                           ub.2                                                   CH.sub.3                                                                            CH.sub.3                                                                              H        (CH.sub.2).sub.3CH(SCH.sub.3)CH.sub.2                  CH.sub.3                                                                            CH.sub.3                                                                              H        (CH.sub.2).sub.2CH(SCH.sub.3)(CH.sub.2).sub.2          CH.sub.3                                                                            CH.sub.3                                                                              H                                                                                       ##STR41##                                             CH.sub.3                                                                            CH.sub.3                                                                              H                                                                                       ##STR42##                                             CH.sub.3                                                                            CH.sub.3                                                                              H                                                                                       ##STR43##                                             CH.sub.3                                                                            CH.sub.3                                                                              H                                                                                       ##STR44##                                             CH.sub.3                                                                            CH.sub.3                                                                              H                                                                                       ##STR45##                                             CH.sub.3                                                                            CH.sub.3                                                                              H                                                                                       ##STR46##                                             CH.sub.3                                                                            CH.sub.3                                                                              H                                                                                       ##STR47##                                             CH.sub.3                                                                            CH.sub.3                                                                              H                                                                                       ##STR48##                                             CH.sub.3                                                                            CH.sub.3                                                                              6-CH.sub.3                                                                             (CH.sub.2).sub.4CH(OCH.sub.3)                          CH.sub.3                                                                            CH.sub.3                                                                              6-CH.sub.3                                                                             (CH.sub.2).sub.3CH(OCH.sub.3)CH.sub.2                  CH.sub.3                                                                            CH.sub.3                                                                              6-CH.sub.3                                                                             (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2          CH.sub.3                                                                            CH.sub.3                                                                              6-CH.sub.3                                                                             (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.                           2                                                      CH.sub.3                                                                            CH.sub.3                                                                              6-CH.sub.3                                                                             (CH.sub.2).sub.2CH(OC.sub.3 H.sub.7)(CH.sub.2).sub.                           2                                                      CH.sub.3                                                                            CH.sub.3                                                                              6-CH.sub.3                                                                             (CH.sub.2).sub.2CH(O-i-C.sub.3 H.sub.7)(CH.sub.2).s                           ub.2                                                   CH.sub.3                                                                            CH.sub.3                                                                              6-CH.sub.3                                                                             (CH.sub.2).sub.2CH(O-t-C.sub.4 H.sub.9)(CH.sub.2).s                           ub.2                                                   CH.sub.3                                                                            CH.sub.3                                                                              6-CH.sub.3                                                                             (CH.sub.2).sub.3CH(SCH.sub.3)CH.sub.2                  CH.sub.3                                                                            CH.sub.3                                                                              6-CH.sub.3                                                                             (CH.sub.2).sub.2CH(SCH.sub.3)(CH.sub.2).sub.2          CH.sub.3                                                                            CH.sub.3                                                                              6-CH.sub.3                                                                              ##STR49##                                             CH.sub.3                                                                            CH.sub.3                                                                              6-CH.sub.3                                                                              ##STR50##                                             CH.sub.3                                                                            CH.sub.3                                                                              6-CH.sub.3                                                                              ##STR51##                                             CH.sub.3                                                                            CH.sub.3                                                                              6-CH.sub.3                                                                              ##STR52##                                             CH.sub.3                                                                            CH.sub.3                                                                              6-CH.sub.3                                                                              ##STR53##                                             CH.sub.3                                                                            CH.sub.3                                                                              6-CH.sub.3                                                                              ##STR54##                                             CH.sub.3                                                                            CH.sub.3                                                                              6-CH.sub.3                                                                              ##STR55##                                             CH.sub.3                                                                            CH.sub.3                                                                              6-CH.sub.3                                                                              ##STR56##                                             ______________________________________                                    

The following 3-aryl-4-hydroxy-Δ³ -dihydrofuranone derivatives of theformula (Ib) may be mentioned individually in addition to the compoundsmentioned in the preparation examples:

                                      TABLE 2                                     __________________________________________________________________________     ##STR57##                                                                    X  Y  Z.sub.n                                                                           A    B           R.sup.1                                            __________________________________________________________________________    Cl Cl H   (CH.sub.2).sub.4CH(OCH.sub.3)                                                                  CH.sub.3                                           Cl Cl H   (CH.sub.2).sub.3CH(OCH.sub.3)CH.sub.2                                                          CH.sub.3                                           Cl Cl H   (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  CH.sub.3                                           Cl Cl H   (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                           CH.sub.3                                           Cl Cl H   (CH.sub.2).sub.2CH(OC.sub.3 H.sub.7)(CH.sub.2).sub.2                                           CH.sub.3                                           Cl Cl H   (CH.sub.2).sub.2CH(O-i-C.sub.3 H.sub.7)(CH.sub.2).sub.2                                        CH.sub.3                                           Cl Cl H   (CH.sub.2).sub.2CH(O-t-C.sub.4 H.sub.9)(CH.sub.2).sub.2                                        CH.sub.3                                           Cl Cl H   (CH.sub.2).sub.3CH(SCH.sub.3)CH.sub.2                                                          CH.sub.3                                           Cl Cl H   (CH.sub.2).sub.2CH(SCH.sub.3)(CH.sub.2).sub.2                                                  CH.sub.3                                           Cl Cl H                                                                                  ##STR58##       CH.sub.3                                           Cl Cl H                                                                                  ##STR59##       CH.sub.3                                           Cl Cl H                                                                                  ##STR60##       CH.sub.3                                           Cl Cl H                                                                                  ##STR61##       CH.sub.3                                           Cl Cl H                                                                                  ##STR62##       CH.sub.3                                           Cl Cl H                                                                                  ##STR63##       CH.sub.3                                           Cl Cl H                                                                                  ##STR64##       CH.sub.3                                           Cl Cl H                                                                                  ##STR65##       CH.sub.3                                           Cl Cl H   (CH.sub.2).sub.4CH(OCH.sub.3)                                                                  i-C.sub.3 H.sub.7                                  Cl Cl H   (CH.sub.2).sub.3CH(OCH.sub.3)CH.sub.2                                                          i-C.sub.3 H.sub.7                                  Cl Cl H   (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  i-C.sub.3 H.sub.7                                  Cl Cl H   (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                           i-C.sub.3 H.sub.7                                  Cl Cl H   (CH.sub.2).sub.2CH(OC.sub.3 H.sub.7)(CH.sub.2).sub.2                                           i-C.sub.3 H.sub.7                                  Cl Cl H   (CH.sub.2).sub.2CH(O-i-C.sub.3 H.sub.7)(CH.sub.2).sub.2                                        i-C.sub.3 H.sub.7                                  Cl Cl H   (CH.sub.2).sub.2CH(O-t-C.sub.4 H.sub.9)(CH.sub.2).sub.2                                        i-C.sub.3 H.sub.7                                  Cl Cl H   (CH.sub.2).sub.3CH(SCH.sub.3)CH.sub.2                                                          i-C.sub.3 H.sub.7                                  Cl Cl H   (CH.sub.2).sub.2CH(SCH.sub.3)(CH.sub.2).sub.2                                                  i-C.sub.3 H.sub.7                                  Cl Cl H                                                                                  ##STR66##       i-C.sub.3 H.sub.7                                  Cl Cl H                                                                                  ##STR67##       i-C.sub.3 H.sub.7                                  Cl Cl H                                                                                  ##STR68##       i-C.sub.3 H.sub.7                                  Cl Cl H                                                                                  ##STR69##       i-C.sub.3 H.sub.7                                  Cl Cl H                                                                                  ##STR70##       i-C.sub.3 H.sub.7                                  Cl Cl H                                                                                  ##STR71##       i-C.sub.3 H.sub.7                                  Cl Cl H                                                                                  ##STR72##       i-C.sub.3 H.sub.7                                  Cl Cl H                                                                                  ##STR73##       i-C.sub.3 H.sub.7                                  Cl Cl H   (CH.sub.2).sub.4CH(OCH.sub.3)                                                                  t-C.sub.4 H.sub.9                                  Cl Cl H   (CH.sub.2).sub.3CH(OCH.sub.3)CH.sub.2                                                          t-C.sub.4 H.sub.9                                  Cl Cl H   (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  t-C.sub.4 H.sub.9                                  Cl Cl H   (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                           t-C.sub.4 H.sub.9                                  Cl Cl H   (CH.sub.2).sub.2CH(OC.sub.3 H.sub.7)(CH.sub.2).sub.2                                           t-C.sub.4 H.sub.9                                  Cl Cl H   (CH.sub.2).sub.2CH(O-i-C.sub.3 H.sub.7)(CH.sub.2).sub.2                                        t-C.sub.4 H.sub.9                                  Cl Cl H   (CH.sub.2).sub.2CH(O-t-C.sub.4 H.sub.9)(CH.sub.2).sub.2                                        t-C.sub.4 H.sub.9                                  Cl Cl H   (CH.sub.2).sub.3CH(SCH.sub.3)CH.sub.2                                                          t-C.sub.4 H.sub.9                                  Cl Cl H   (CH.sub.2).sub.2CH(SCH.sub.3)(CH.sub.2).sub.2                                                  t-C.sub.4 H.sub.9                                  Cl Cl H                                                                                  ##STR74##       t-C.sub.4 H.sub.9                                  Cl Cl H                                                                                  ##STR75##       t-C.sub.4 H.sub.9                                  Cl Cl H                                                                                  ##STR76##       t-C.sub.4 H.sub.9                                  Cl Cl H                                                                                  ##STR77##       t-C.sub.4 H.sub.9                                  Cl Cl H                                                                                  ##STR78##       t-C.sub.4 H.sub.9                                  Cl Cl H                                                                                  ##STR79##       t-C.sub.4 H.sub.9                                  Cl Cl H                                                                                  ##STR80##       t-C.sub.4 H.sub.9                                  Cl Cl H                                                                                  ##STR81##       t-C.sub.4 H.sub.9                                  Cl Cl H   (CH.sub.2).sub.4CH(OCH.sub.3)                                                                  (CH.sub.3).sub.2 CH.sub.2 Cl                       Cl Cl H   (CH.sub.2).sub.3CH(OCH.sub.3)CH.sub.2                                                          (CH.sub.3).sub.2 CH.sub.2 Cl                       Cl Cl H   (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  (CH.sub.3).sub.2 CH.sub.2 Cl                       Cl Cl H   (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                           (CH.sub.3).sub.2 CH.sub.2 Cl                       Cl Cl H   (CH.sub.2).sub.2CH(OC.sub.3 H.sub.7)(CH.sub.2).sub.2                                           (CH.sub.3).sub.2 CH.sub.2 Cl                       Cl Cl H   (CH.sub.2).sub.2CH(O-i-C.sub.3 H.sub.7)(CH.sub.2).sub.2                                        C(CH.sub.3).sub.2 CH.sub.2 Cl                      Cl Cl H   (CH.sub.2).sub.2CH(O-t-C.sub.4 H.sub.9)(CH.sub.2).sub.2                                        C(CH.sub.3).sub.2 CH.sub.2 Cl                      Cl Cl H   (CH.sub.2).sub.3CH(SCH.sub.3)CH.sub.2                                                          C(CH.sub.3).sub.2 CH.sub.2 Cl                      Cl Cl H   (CH.sub.2).sub.2CH(SCH.sub.3)(CH.sub.2).sub.2                                                  C(CH.sub.3).sub.2 CH.sub.2 Cl                      Cl Cl H                                                                                  ##STR82##       C(CH.sub.3).sub.2 CH.sub.2 Cl                      Cl Cl H                                                                                  ##STR83##       C(CH.sub.3).sub.2 CH.sub.2 Cl                      Cl Cl H                                                                                  ##STR84##       C(CH.sub.3).sub.2 CH.sub.2 Cl                      Cl Cl H                                                                                  ##STR85##       C(CH.sub.3).sub.2 CH.sub.2 Cl                      Cl Cl H                                                                                  ##STR86##       C(CH.sub.3).sub.2 CH.sub.2 Cl                      Cl Cl H                                                                                  ##STR87##       C(CH.sub.3).sub.2 CH.sub.2 Cl                      Cl Cl H                                                                                  ##STR88##       C(CH.sub.3).sub.2 CH.sub.2 Cl                      Cl Cl H                                                                                  ##STR89##       C(CH.sub.3).sub.2 CH.sub.2 Cl                      Cl Cl H   (CH.sub.2).sub.4CH(OCH.sub.3)                                                                  C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                Cl Cl H   (CH.sub.2).sub.3CH(OCH.sub.3)CH.sub.2                                                          C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                Cl Cl H   (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                Cl Cl H   (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                           C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                Cl Cl H   (CH.sub.2).sub.2CH(OC.sub.3 H.sub.7)(CH.sub.2).sub.2                                           C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                Cl Cl H   (CH.sub.2).sub.2CH(O-i-C.sub.3 H.sub.7)(CH.sub.2).sub.2                                        C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                Cl Cl H   (CH.sub.2).sub.2CH(O-t-C.sub.4 H.sub.9)(CH.sub.2).sub.2                                        C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                Cl Cl H   (CH.sub.2).sub.3CH(SCH.sub.3)CH.sub.2                                                          C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                Cl Cl H   (CH.sub.2).sub.2CH(SCH.sub.3)(CH.sub.2).sub.2                                                  C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                Cl Cl H                                                                                  ##STR90##       C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                Cl Cl H                                                                                  ##STR91##       C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                Cl Cl H                                                                                  ##STR92##       C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                Cl Cl H                                                                                  ##STR93##       C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                Cl Cl H                                                                                  ##STR94##       C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                Cl Cl H                                                                                  ##STR95##       C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                Cl Cl H                                                                                  ##STR96##       C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                Cl Cl H                                                                                  ##STR97##       C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                CH.sub.3                                                                         CH.sub.3                                                                         H   (CH.sub.2).sub.4CH(OCH.sub.3)                                                                  CH.sub.3                                           CH.sub.3                                                                         CH.sub.3                                                                         H   (CH.sub.2).sub.3CH(OCH.sub.3)CH.sub.2                                                          CH.sub.3                                           CH.sub.3                                                                         CH.sub.3                                                                         H   (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  CH.sub.3                                           CH.sub.3                                                                         CH.sub.3                                                                         H   (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                           CH.sub.3                                           CH.sub.3                                                                         CH.sub.3                                                                         H   (CH.sub.2).sub.2CH(OC.sub.3 H.sub.7)(CH.sub.2).sub.2                                           CH.sub.3                                           CH.sub.3                                                                         CH.sub.3                                                                         H   (CH.sub.2).sub.2CH(O-i-C.sub.3 H.sub.7)(CH.sub.2).sub.2                                        CH.sub.3                                           CH.sub.3                                                                         CH.sub.3                                                                         H   (CH.sub.2).sub.2CH(O-t-C.sub.4 H.sub.9)(CH.sub.2).sub.2                                        CH.sub.3                                           CH.sub.3                                                                         CH.sub.3                                                                         H   (CH.sub.2).sub.3CH(SCH.sub.3)CH.sub.2                                                          CH.sub.3                                           CH.sub.3                                                                         CH.sub.3                                                                         H   (CH.sub.2).sub.2CH(SCH.sub.3)(CH.sub.2).sub.2                                                  CH.sub.3                                           CH.sub.3                                                                         CH.sub.3                                                                         H                                                                                  ##STR98##       CH.sub.3                                           CH.sub.3                                                                         CH.sub.3                                                                         H                                                                                  ##STR99##       CH.sub.3                                           CH.sub.3                                                                         CH.sub.3                                                                         H                                                                                  ##STR100##      CH.sub.3                                           CH.sub.3                                                                         CH.sub.3                                                                         H                                                                                  ##STR101##      CH.sub.3                                           CH.sub.3                                                                         CH.sub.3                                                                         H                                                                                  ##STR102##      CH.sub.3                                           CH.sub.3                                                                         CH.sub.3                                                                         H                                                                                  ##STR103##      CH.sub.3                                           CH.sub.3                                                                         CH.sub.3                                                                         H                                                                                  ##STR104##      CH.sub.3                                           CH.sub.3                                                                         CH.sub.3                                                                         H                                                                                  ##STR105##      CH.sub.3                                           CH.sub.3                                                                         CH.sub.3                                                                         H   (CH.sub.2).sub.4CH(OCH.sub.3)                                                                  i-C.sub.3 H.sub.7                                  CH.sub.3                                                                         CH.sub.3                                                                         H   (CH.sub.2).sub.3CH(OCH.sub.3)CH.sub.2                                                          i-C.sub.3 H.sub.7                                  CH.sub.3                                                                         CH.sub.3                                                                         H   (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  i-C.sub.3 H.sub.7                                  CH.sub.3                                                                         CH.sub.3                                                                         H   (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                           i-C.sub.3 H.sub.7                                  CH.sub.3                                                                         CH.sub.3                                                                         H   (CH.sub.2).sub.2CH(OC.sub.3 H.sub.7)(CH.sub.2).sub.2                                           i-C.sub.3 H.sub.7                                  CH.sub.3                                                                         CH.sub.3                                                                         H   (CH.sub.2).sub.2CH(O-i-C.sub.3 H.sub.7)(CH.sub.2).sub.2                                        i-C.sub.3 H.sub.7                                  CH.sub.3                                                                         CH.sub.3                                                                         H   (CH.sub.2).sub.2CH(O-t-C.sub.4 H.sub.9)(CH.sub.2).sub.2                                        i-C.sub.3 H.sub.7                                  CH.sub.3                                                                         CH.sub.3                                                                         H   (CH.sub.2).sub.3CH(SCH.sub.3)CH.sub.2                                                          i-C.sub.3 H.sub.7                                  CH.sub.3                                                                         CH.sub.3                                                                         H   (CH.sub.2).sub.2CH(SCH.sub.3)(CH.sub.2).sub.2                                                  i-C.sub.3 H.sub.7                                  CH.sub.3                                                                         CH.sub.3                                                                         H                                                                                  ##STR106##      i-C.sub.3 H.sub.7                                  CH.sub.3                                                                         CH.sub.3                                                                         H                                                                                  ##STR107##      i-C.sub.3 H.sub.7                                  CH.sub.3                                                                         CH.sub.3                                                                         H                                                                                  ##STR108##      i-C.sub.3 H.sub.7                                  CH.sub.3                                                                         CH.sub.3                                                                         H                                                                                  ##STR109##      i-C.sub.3 H.sub.7                                  CH.sub.3                                                                         CH.sub.3                                                                         H                                                                                  ##STR110##      i-C.sub.3 H.sub.7                                  CH.sub.3                                                                         CH.sub.3                                                                         H                                                                                  ##STR111##      i-C.sub.3 H.sub.7                                  CH.sub.3                                                                         CH.sub.3                                                                         H                                                                                  ##STR112##      i-C.sub.3 H.sub.7                                  CH.sub.3                                                                         CH.sub.3                                                                         H                                                                                  ##STR113##      i-C.sub.3 H.sub.7                                  CH.sub.3                                                                         CH.sub.3                                                                         H   (CH.sub.2).sub.4CH(OCH.sub.3)                                                                  t-C.sub.4 H.sub.9                                  CH.sub.3                                                                         CH.sub.3                                                                         H   (CH.sub.2).sub.3CH(OCH.sub.3)CH.sub.2                                                          t-C.sub.4 H.sub.9                                  CH.sub.3                                                                         CH.sub.3                                                                         H   (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  t-C.sub.4 H.sub.9                                  CH.sub.3                                                                         CH.sub.3                                                                         H   (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                           t-C.sub.4 H.sub.9                                  CH.sub.3                                                                         CH.sub.3                                                                         H   (CH.sub.2).sub.2CH(OC.sub.3 H.sub.7)(CH.sub.2).sub.2                                           t-C.sub.4 H.sub.9                                  CH.sub.3                                                                         CH.sub.3                                                                         H   (CH.sub.2).sub.2CH(O-i-C.sub.3 H.sub.7)(CH.sub.2).sub.2                                        t-C.sub.4 H.sub.9                                  CH.sub.3                                                                         CH.sub.3                                                                         H   (CH.sub.2).sub.2CH(O-t-C.sub.4 H.sub.9)(CH.sub.2).sub.2                                        t-C.sub.4 H.sub.9                                  CH.sub.3                                                                         CH.sub.3                                                                         H   (CH.sub.2).sub.3CH(SCH.sub.3)CH.sub.2                                                          t-C.sub.4 H.sub.9                                  CH.sub.3                                                                         CH.sub.3                                                                         H   (CH.sub.2).sub.2CH(SCH.sub.3)(CH.sub.2).sub.2                                                  t-C.sub.4 H.sub.9                                  CH.sub.3                                                                         CH.sub.3                                                                         H                                                                                  ##STR114##      t-C.sub.4 H.sub.9                                  CH.sub.3                                                                         CH.sub.3                                                                         H                                                                                  ##STR115##      t-C.sub.4 H.sub.9                                  CH.sub.3                                                                         CH.sub.3                                                                         H                                                                                  ##STR116##      t-C.sub.4 H.sub.9                                  CH.sub.3                                                                         CH.sub.3                                                                         H                                                                                  ##STR117##      t-C.sub.4 H.sub.9                                  CH.sub.3                                                                         CH.sub.3                                                                         H                                                                                  ##STR118##      t-C.sub.4 H.sub.9                                  CH.sub.3                                                                         CH.sub.3                                                                         H                                                                                  ##STR119##      t-C.sub.4 H.sub.9                                  CH.sub.3                                                                         CH.sub.3                                                                         H                                                                                  ##STR120##      t-C.sub.4 H.sub.9                                  CH.sub.3                                                                         CH.sub.3                                                                         H                                                                                  ##STR121##      t-C.sub.4 H.sub.9                                  CH.sub.3                                                                         CH.sub.3                                                                         H   (CH.sub.2).sub.4CH(OCH.sub.3)                                                                  C(CH.sub.3).sub.2 CH.sub.2 Cl                      CH.sub.3                                                                         CH.sub.3                                                                         H   (CH.sub.2).sub.3CH(OCH.sub.3)CH.sub.2                                                          C(CH.sub.3).sub.2 CH.sub.2 Cl                      CH.sub.3                                                                         CH.sub.3                                                                         H   (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  C(CH.sub.3).sub.2 CH.sub.2 Cl                      CH.sub.3                                                                         CH.sub.3                                                                         H   (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                           C(CH.sub.3).sub.2 CH.sub.2 Cl                      CH.sub.3                                                                         CH.sub.3                                                                         H   (CH.sub.2).sub.2CH(OC.sub.3 H.sub.7)(CH.sub.2).sub.2                                           C(CH.sub.3).sub.2 CH.sub.2 Cl                      CH.sub.3                                                                         CH.sub.3                                                                         H   (CH.sub.2).sub.2CH(O-i-C.sub.3 H.sub.7)(CH.sub.2).sub.2                                        C(CH.sub.3).sub.2 CH.sub.2 Cl                      CH.sub.3                                                                         CH.sub.3                                                                         H   (CH.sub.2).sub.2CH(O-t-C.sub.4 H.sub.9)(CH.sub.2).sub.2                                        C(CH.sub.3).sub.2 CH.sub.2 Cl                      CH.sub.3                                                                         CH.sub.3                                                                         H   (CH.sub.2).sub.3CH(SCH.sub.3)CH.sub.2                                                          C(CH.sub.3).sub.2 CH.sub.2 Cl                      CH.sub.3                                                                         CH.sub.3                                                                         H   (CH.sub.2).sub.2CH(SCH.sub.3)(CH.sub.2).sub.2                                                  C(CH.sub.3).sub.2 CH.sub.2 Cl                      CH.sub.3                                                                         CH.sub.3                                                                         H                                                                                  ##STR122##      C(CH.sub.3).sub.2 CH.sub.2 Cl                      CH.sub.3                                                                         CH.sub.3                                                                         H                                                                                  ##STR123##      C(CH.sub.3).sub.2 CH.sub.2 Cl                      CH.sub.3                                                                         CH.sub.3                                                                         H                                                                                  ##STR124##      C(CH.sub.3).sub.2 CH.sub.2 Cl                      CH.sub.3                                                                         CH.sub.3                                                                         H                                                                                  ##STR125##      C(CH.sub.3).sub.2 CH.sub.2 Cl                      CH.sub.3                                                                         CH.sub.3                                                                         H                                                                                  ##STR126##      C(CH.sub.3).sub.2 CH.sub.2 Cl                      CH.sub.3                                                                         CH.sub.3                                                                         H                                                                                  ##STR127##      C(CH.sub.3).sub.2 CH.sub.2 Cl                      CH.sub.3                                                                         CH.sub.3                                                                         H                                                                                  ##STR128##      C(CH.sub.3).sub.2 CH.sub.2 Cl                      CH.sub.3                                                                         CH.sub.3                                                                         H                                                                                  ##STR129##      C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                CH.sub.3                                                                         CH.sub.3                                                                         H   (CH.sub.2).sub.4CH(OCH.sub.3)                                                                  C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                CH.sub.3                                                                         CH.sub.3                                                                         H   (CH.sub.2).sub.3CH(OCH.sub.3)CH.sub.2                                                          C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                CH.sub.3                                                                         CH.sub.3                                                                         H   (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                CH.sub.3                                                                         CH.sub.3                                                                         H   (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                           C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                CH.sub.3                                                                         CH.sub.3                                                                         H   (CH.sub.2).sub.2CH(OC.sub.3 H.sub.7)(CH.sub.2).sub.2                                           C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                CH.sub.3                                                                         CH.sub.3                                                                         H   (CH.sub.2).sub.2CH(O-i-C.sub.3 H.sub.7)(CH.sub.2).sub.2                                        C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                CH.sub.3                                                                         CH.sub.3                                                                         H   (CH.sub.2).sub.2CH(O-t-C.sub.4 H.sub.9)(CH.sub.2).sub.2                                        C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                CH.sub.3                                                                         CH.sub.3                                                                         H   (CH.sub.2).sub.3CH(SCH.sub.3)CH.sub.2                                                          C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                CH.sub.3                                                                         CH.sub.3                                                                         H   (CH.sub.2).sub.2CH(SCH.sub.3)(CH.sub.2).sub.2                                                  C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                CH.sub.3                                                                         CH.sub.3                                                                         H                                                                                  ##STR130##      C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                CH.sub.3                                                                         CH.sub.3                                                                         H                                                                                  ##STR131##      C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                CH.sub.3                                                                         CH.sub.3                                                                         H                                                                                  ##STR132##      C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                CH.sub.3                                                                         CH.sub.3                                                                         H                                                                                  ##STR133##      C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                CH.sub.3                                                                         CH.sub.3                                                                         H                                                                                  ##STR134##      C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                CH.sub.3                                                                         CH.sub.3                                                                         H                                                                                  ##STR135##      C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                CH.sub.3                                                                         CH.sub.3                                                                         H                                                                                  ##STR136##      C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                CH.sub.3                                                                         CH.sub.3                                                                         H                                                                                  ##STR137##      C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.4CH(OCH.sub.3)                                                                  CH.sub.3                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.3CH(OCH.sub.3)CH.sub.2                                                          CH.sub.3                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  CH.sub.3                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                           CH.sub.3                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OC.sub.3 H.sub.7)(CH.sub.2).sub.2                                           CH.sub.3                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(O-i-C.sub.3 H.sub.7)(CH.sub.2).sub.2                                        CH.sub.3                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(O-t-C.sub.4 H.sub.9)(CH.sub.2).sub.2                                        CH.sub.3                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.3CH(SCH.sub.3)CH.sub.2                                                          CH.sub.3                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(SCH.sub.3)(CH.sub.2).sub.2                                                  CH.sub.3                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR138##      CH.sub.3                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR139##      CH.sub.3                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR140##      CH.sub.3                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR141##      CH.sub.3                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR142##      CH.sub.3                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR143##      CH.sub.3                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR144##      CH.sub.3                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR145##      CH.sub.3                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.4CH(OCH.sub.3)                                                                  i-C.sub.3 H.sub.7                                  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.3CH(OCH.sub.3)CH.sub.2                                                          i-C.sub.3 H.sub.7                                  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  i-C.sub.3 H.sub.7                                  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                           i-C.sub.3 H.sub.7                                  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OC.sub.3 H.sub.7)(CH.sub.2).sub.2                                           i-C.sub.3 H.sub.7                                  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(O-i-C.sub.3 H.sub.7)(CH.sub.2).sub.2                                        i-C.sub.3 H.sub.7                                  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(O-t-C.sub.4 H.sub.9)(CH.sub.2).sub.2                                        i-C.sub.3 H.sub.7                                  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.3CH(SCH.sub.3)CH.sub.2                                                          i-C.sub.3 H.sub.7                                  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(SCH.sub.3)(CH.sub.2).sub.2                                                  i-C.sub.3 H.sub.7                                  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR146##      i-C.sub.3 H.sub.7                                  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR147##      i-C.sub.3 H.sub.7                                  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR148##      i-C.sub.3 H.sub.7                                  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR149##      i-C.sub.3 H.sub.7                                  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR150##      i-C.sub.3 H.sub.7                                  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR151##      i-C.sub.3 H.sub.7                                  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR152##      i-C.sub.3 H.sub.7                                  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR153##      i-C.sub.3 H.sub.7                                  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.4CH(OCH.sub.3)                                                                  t-C.sub.4 H.sub.9                                  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.3CH(OCH.sub.3)CH.sub.2                                                          t-C.sub.4 H.sub.9                                  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  t-C.sub.4 H.sub.9                                  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                           t-C.sub.4 H.sub.9                                  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OC.sub.3 H.sub.7)(CH.sub.2).sub.2                                           t-C.sub.4 H.sub.9                                  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(O-i-C.sub.3 H.sub.7)(CH.sub.2).sub.2                                        t-C.sub.4 H.sub.9                                  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(O-t-C.sub.4 H.sub.9)(CH.sub.2).sub.2                                        t-C.sub.4 H.sub.9                                  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.3CH(SCH.sub.3)CH.sub.2                                                          t-C.sub.4 H.sub.9                                  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(SCH.sub.3)(CH.sub.2).sub.2                                                  t-C.sub.4 H.sub.9                                  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR154##      t-C.sub.4 H.sub.9                                  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR155##      t-C.sub.4 H.sub.9                                  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR156##      t-C.sub.4 H.sub.9                                  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR157##      t-C.sub.4 H.sub.9                                  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR158##      t-C.sub.4 H.sub.9                                  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR159##      t-C.sub.4 H.sub.9                                  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR160##      t-C.sub.4 H.sub.9                                  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR161##      t-C.sub.4 H.sub.9                                  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.4CH(OCH.sub.3)                                                                  C(CH.sub.3).sub.2 CH.sub.2 Cl                      CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.3CH(OCH.sub.3)CH.sub.2                                                          C(CH.sub.3).sub.2 CH.sub.2 Cl                      CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  C(CH.sub.3).sub.2 CH.sub.2 Cl                      CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                           C(CH.sub.3).sub.2 CH.sub.2 Cl                      CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OC.sub.3 H.sub.7)(CH.sub.2).sub.2                                           C(CH.sub.3).sub.2 CH.sub.2 Cl                      CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(O-i-C.sub.3 H.sub.7)(CH.sub.2).sub.2                                        C(CH.sub.3).sub.2 CH.sub.2 Cl                      CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(O-t-C.sub.4 H.sub.9)(CH.sub.2).sub.2                                        C(CH.sub.3).sub.2 CH.sub.2 Cl                      CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.3CH(SCH.sub.3)CH.sub.2                                                          C(CH.sub.3).sub.2 CH.sub.2 Cl                      CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(SCH.sub.3)(CH.sub.2).sub.2                                                  C(CH.sub.3).sub.2 CH.sub.2 Cl                      CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR162##      C(CH.sub.3).sub.2 CH.sub.2 Cl                      CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR163##      C(CH.sub.3).sub.2 CH.sub.2 Cl                      CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR164##      C(CH.sub.3).sub.2 CH.sub.2 Cl                      CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR165##      C(CH.sub.3).sub.2 CH.sub.2 Cl                      CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR166##      C(CH.sub.3).sub.2 CH.sub.2 Cl                      CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR167##      C(CH.sub.3).sub.2 CH.sub.2 Cl                      CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR168##      C(CH.sub.3).sub.2 CH.sub.2 Cl                      CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR169##      C(CH.sub.3).sub.2 CH.sub.2 Cl                      CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.4CH(OCH.sub.3)                                                                  C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.3CH(OCH.sub.3)CH.sub.2                                                          C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                           C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OC.sub.3 H.sub.7)(CH.sub.2).sub.2                                           C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(O-i-C.sub.3 H.sub.7)(CH.sub.2).sub.2                                        C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(O-t-C.sub.4 H.sub.9)(CH.sub.2).sub.2                                        C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.3CH(SCH.sub.3)CH.sub.2                                                          C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(SCH.sub.3)(CH.sub.2).sub.2                                                  C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR170##      C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR171##      C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR172##      C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR173##      C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR174##      C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR175##      C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR176##      C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR177##      C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                __________________________________________________________________________

The following 3-aryl-4-hydroxy-Δ³ -dihydrofuranone derivatives of theformula (Ic) may be mentioned individually in addition to the compoundsmentioned in the preparation examples:

                                      TABLE 3                                     __________________________________________________________________________     ##STR178##                                                                   X   Y  Z.sub.n                                                                            A    B           L  M R.sup.2                                     __________________________________________________________________________    Cl  Cl H    (CH.sub.2).sub.4CH(OCH.sub.3)                                                                  O  O C.sub.2 H.sub.5                             Cl  Cl H    (CH.sub.2).sub.3CH(OCH.sub.3)CH.sub.2                                                          O  O C.sub.2 H.sub.5                             Cl  Cl H    (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  O  O C.sub.2 H.sub.5                             Cl  Cl H    (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                           O  O C.sub.2 H.sub.5                             Cl  Cl H    (CH.sub.2).sub.2CH(OC.sub.3 H.sub.7)(CH.sub.2).sub.2                                           O  O C.sub.2 H.sub.5                             Cl  Cl H    (CH.sub.2).sub.2CH(O-i-C.sub.3 H.sub.7)(CH.sub.2).sub.2                                        O  O C.sub.2 H.sub.5                             Cl  Cl H    (CH.sub.2).sub.2CH(O-t-C.sub.4 H.sub.9)(CH.sub.2).sub.2                                        O  O C.sub.2 H.sub.5                             Cl  Cl H    (CH.sub.2).sub.3CH(SCH.sub.3)CH.sub.2                                                          O  O C.sub.2 H.sub.5                             Cl  Cl H    (CH.sub.2).sub.2CH(SCH.sub.3)(CH.sub.2).sub.2                                                  O  O C.sub.2 H.sub.5                             Cl  Cl H                                                                                   ##STR179##      O  O C.sub.2 H.sub.5                             Cl  Cl H                                                                                   ##STR180##      O  O C.sub.2 H.sub.5                             Cl  Cl H                                                                                   ##STR181##      O  O C.sub.2 H.sub.5                             Cl  Cl H                                                                                   ##STR182##      O  O C.sub.2 H.sub.5                             Cl  Cl H                                                                                   ##STR183##      O  O C.sub.2 H.sub.5                             Cl  Cl H                                                                                   ##STR184##      O  O C.sub.2 H.sub.5                             Cl  Cl H                                                                                   ##STR185##      O  O C.sub.2 H.sub.5                             Cl  Cl H                                                                                   ##STR186##      O  O C.sub.2 H.sub.5                             Cl  Cl H    (CH.sub.2).sub.4CH(OCH.sub.3)                                                                  O  O i-C.sub.3 H.sub.7                           Cl  Cl H    (CH.sub.2).sub.3CH(OCH.sub.3)CH.sub.2                                                          O  O i-C.sub.3 H.sub.7                           Cl  Cl H    (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  O  O i-C.sub.3 H.sub.7                           Cl  Cl H    (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                           O  O i-C.sub.3 H.sub.7                           Cl  Cl H    (CH.sub.2).sub.2CH(OC.sub.3 H.sub.7)(CH.sub.2).sub.2                                           O  O i-C.sub.3 H.sub.7                           Cl  Cl H    (CH.sub.2).sub.2CH(O-i-C.sub.3 H.sub.7)(CH.sub.2).sub.2                                        O  O i-C.sub.3 H.sub.7                           Cl  Cl H    (CH.sub.2).sub.2CH(O-t-C.sub.4 H.sub.9)(CH.sub.2).sub.2                                        O  O i-C.sub.3 H.sub.7                           Cl  Cl H    (CH.sub.2).sub.3CH(SCH.sub.3)CH.sub.2                                                          O  O i-C.sub.3 H.sub.7                           Cl  Cl H    (CH.sub.2).sub.2CH(SCH.sub.3)(CH.sub.2).sub.2                                                  O  O i-C.sub.3 H.sub.7                           Cl  Cl H                                                                                   ##STR187##      O  O i-C.sub.3 H.sub.7                           Cl  Cl H                                                                                   ##STR188##      O  O i-C.sub.3 H.sub.7                           Cl  Cl H                                                                                   ##STR189##      O  O i-C.sub.3 H.sub.7                           Cl  Cl H                                                                                   ##STR190##      O  O i-C.sub.3 H.sub.7                           Cl  Cl H                                                                                   ##STR191##      O  O i-C.sub.3 H.sub.7                           Cl  Cl H                                                                                   ##STR192##      O  O i-C.sub.3 H.sub.7                           Cl  Cl H                                                                                   ##STR193##      O  O i-C.sub.3 H.sub.7                           Cl  Cl H                                                                                   ##STR194##      O  O i-C.sub.3 H.sub.7                           Cl  Cl H    (CH.sub.2).sub.4CH(OCH.sub.3)                                                                  O  S i-C.sub.3 H.sub.7                           Cl  Cl H    (CH.sub.2).sub.3CH(OCH.sub.3)CH.sub.2                                                          O  S i-C.sub.3 H.sub.7                           Cl  Cl H    (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  O  S i-C.sub.3 H.sub.7                           Cl  Cl H    (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                           O  S i-C.sub.3 H.sub.7                           Cl  Cl H    (CH.sub.2).sub.2CH(OC.sub.3 H.sub.7)(CH.sub.2).sub.2                                           O  S i-C.sub.3 H.sub.7                           Cl  Cl H    (CH.sub.2).sub.2CH(O-i-C.sub.3 H.sub.7)(CH.sub.2).sub.2                                        O  S i-C.sub.3 H.sub.7                           Cl  Cl H    (CH.sub.2).sub.2CH(O-t-C.sub.4 H.sub.9)(CH.sub.2).sub.2                                        O  S i-C.sub.3 H.sub.7                           Cl  Cl H    (CH.sub.2).sub.3CH(SCH.sub.3)CH.sub.2                                                          O  S i-C.sub.3 H.sub.7                           Cl  Cl H    (CH.sub.2).sub.2CH(SCH.sub.3)(CH.sub.2).sub.2                                                  O  S i-C.sub.3 H.sub.7                           Cl  Cl H                                                                                   ##STR195##      O  S i-C.sub.3 H.sub.7                           Cl  Cl H                                                                                   ##STR196##      O  S i-C.sub.3 H.sub.7                           Cl  Cl H                                                                                   ##STR197##      O  S i-C.sub.3 H.sub.7                           Cl  Cl H                                                                                   ##STR198##      O  S i-C.sub.3 H.sub.7                           Cl  Cl H                                                                                   ##STR199##      O  S i-C.sub.3 H.sub.7                           Cl  Cl H                                                                                   ##STR200##      O  S i-C.sub.3 H.sub.7                           Cl  Cl H                                                                                   ##STR201##      O  S i-C.sub.3 H.sub.7                           Cl  Cl H                                                                                   ##STR202##      O  S i-C.sub.3 H.sub.7                           Cl  Cl H    (CH.sub.2).sub.4CH(OCH.sub.3)                                                                  O  O i-C.sub.4 H.sub.9                           Cl  Cl H    (CH.sub.2).sub.3CH(OCH.sub.3)CH.sub.2                                                          O  O i-C.sub.4 H.sub.9                           Cl  Cl H    (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  O  O i-C.sub.4 H.sub.9                           Cl  Cl H    (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                           O  O i-C.sub.4 H.sub.9                           Cl  Cl H    (CH.sub.2).sub.2CH(OC.sub.3 H.sub.7)(CH.sub.2).sub.2                                           O  O i-C.sub.4 H.sub.9                           Cl  Cl H    (CH.sub.2).sub.2CH(O-i-C.sub.3 H.sub.7)(CH.sub.2).sub.2                                        O  O i-C.sub.4 H.sub.9                           Cl  Cl H    (CH.sub.2).sub.2CH(O-t-C.sub.4 H.sub.9)(CH.sub.2).sub.2                                        O  O i-C.sub.4 H.sub.9                           Cl  Cl H    (CH.sub.2).sub.3CH(SCH.sub.3)CH.sub.2                                                          O  O i-C.sub.4 H.sub.9                           Cl  Cl H    (CH.sub.2).sub.2CH(SCH.sub.3)(CH.sub.2).sub.2                                                  O  O i-C.sub.4 H.sub.9                           Cl  Cl H                                                                                   ##STR203##      O  O i-C.sub.4 H.sub.9                           Cl  Cl H                                                                                   ##STR204##      O  O i-C.sub.4 H.sub.9                           Cl  Cl H                                                                                   ##STR205##      O  O i-C.sub.4 H.sub.9                           Cl  Cl H                                                                                   ##STR206##      O  O i-C.sub.4 H.sub.9                           Cl  Cl H                                                                                   ##STR207##      O  O i-C.sub.4 H.sub.9                           Cl  Cl H                                                                                   ##STR208##      O  O i-C.sub.4 H.sub.9                           Cl  Cl H                                                                                   ##STR209##      O  O i-C.sub.4 H.sub.7                           Cl  Cl H                                                                                   ##STR210##      O  O i-C.sub.4 H.sub.7                           Cl  Cl H    (CH.sub.2).sub.4CH(OCH.sub.3)                                                                  O  O s-C.sub.4 H.sub.9                           Cl  Cl H    (CH.sub.2).sub.3CH(OCH.sub.3)CH.sub.2                                                          O  O s-C.sub.4 H.sub.9                           Cl  Cl H    (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  O  O s-C.sub.4 H.sub.9                           Cl  Cl H    (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                           O  O s-C.sub.4 H.sub.9                           Cl  Cl H    (CH.sub.2).sub.2CH(OC.sub.3 H.sub.7)(CH.sub.2).sub.2                                           O  O s-C.sub.4 H.sub.9                           Cl  Cl H    (CH.sub.2).sub.2CH(O-i-C.sub.3 H.sub.7)(CH.sub.2).sub.2                                        O  O s-C.sub.4 H.sub.9                           Cl  Cl H    (CH.sub.2).sub.2CH(O-t-C.sub.4 H.sub.9)(CH.sub.2).sub.2                                        O  O s-C.sub.4 H.sub.9                           Cl  Cl H    (CH.sub.2).sub.3CH(SCH.sub.3)CH.sub.2                                                          O  O s-C.sub.4 H.sub.9                           Cl  Cl H    (CH.sub.2).sub.2CH(SCH.sub.3)(CH.sub.2).sub.2                                                  O  O s-C.sub.4 H.sub.9                           Cl  Cl H                                                                                   ##STR211##      O  O s-C.sub.4 H.sub.9                           Cl  Cl H                                                                                   ##STR212##      O  O s-C.sub.4 H.sub.9                           Cl  Cl H                                                                                   ##STR213##      O  O s-C.sub.4 H.sub.9                           Cl  Cl H                                                                                   ##STR214##      O  O s-C.sub.4 H.sub.9                           Cl  Cl H                                                                                   ##STR215##      O  O s-C.sub.4 H.sub.9                           Cl  Cl H                                                                                   ##STR216##      O  O s-C.sub.4 H.sub.9                           Cl  Cl H                                                                                   ##STR217##      O  O s-C.sub.4 H.sub.9                           Cl  Cl H                                                                                   ##STR218##      O  O s-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.4CH(OCH.sub.3)                                                                  O  O C.sub.2 H.sub.5                             CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.3CH(OCH.sub.3)CH.sub.2                                                          O  O C.sub.2 H.sub.5                             CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  O  O C.sub.2 H.sub.5                             CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                           O  O C.sub.2 H.sub.5                             CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.2CH(OC.sub.3 H.sub.7)(CH.sub.2).sub.2                                           O  O C.sub.2 H.sub.5                             CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.2CH(O-i-C.sub.3 H.sub.7)(CH.sub.2).sub.2                                        O  O C.sub.2 H.sub.5                             CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.2CH(O-t-C.sub.4 H.sub.9)(CH.sub.2).sub.2                                        O  O C.sub.2 H.sub.5                             CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.3CH(SCH.sub.3)CH.sub.2                                                          O  O C.sub.2 H.sub.5                             CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.2CH(SCH.sub.3)(CH.sub.2).sub.2                                                  O  O C.sub.2 H.sub.5                             CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR219##      O  O C.sub.2 H.sub.5                             CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR220##      O  O C.sub.2 H.sub.5                             CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR221##      O  O C.sub.2 H.sub.5                             CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR222##      O  O C.sub.2 H.sub.5                             CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR223##      O  O C.sub.2 H.sub.5                             CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR224##      O  O C.sub.2 H.sub.5                             CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR225##      O  O C.sub.2 H.sub.5                             CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR226##      O  O C.sub.2 H.sub.5                             CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.4CH(OCH.sub.3)                                                                  O  O i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.3CH(OCH.sub.3)CH.sub.2                                                          O  O i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  O  O i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                           O  O i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.2CH(OC.sub.3 H.sub.7)(CH.sub.2).sub.2                                           O  O i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.2CH(O-i-C.sub.3 H.sub.7)(CH.sub.2).sub.2                                        O  O i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.2CH(O-t-C.sub.4 H.sub.9)(CH.sub.2).sub.2                                        O  O i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.3CH(SCH.sub.3)CH.sub.2                                                          O  O i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.2CH(SCH.sub.3)(CH.sub.2).sub.2                                                  O  O i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR227##      O  O i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR228##      O  O i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR229##      O  O i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR230##      O  O i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR231##      O  O i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR232##      O  O i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR233##      O  O i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR234##      O  O i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.4CH(OCH.sub.3)                                                                  O  S i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.3CH(OCH.sub.3)CH.sub.2                                                          O  S i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  O  S i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                           O  S i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.2CH(OC.sub.3 H.sub.7)(CH.sub.2).sub.2                                           O  S i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.2CH(O-i-C.sub.3 H.sub.7)(CH.sub.2).sub.2                                        O  S i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.2CH(O-t-C.sub.4 H.sub.9)(CH.sub.2).sub.2                                        O  S i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.3CH(SCH.sub.3)CH.sub.2                                                          O  S i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.2CH(SCH.sub.3)(CH.sub.2).sub.2                                                  O  S i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR235##      O  S i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR236##      O  S i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR237##      O  S i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR238##      O  S i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR239##      O  S i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR240##      O  S i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR241##      O  S i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR242##      O  S i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.4CH(OCH.sub.3)                                                                  O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.3CH(OCH.sub.3)CH.sub.2                                                          O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                           O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.2CH(OC.sub.3 H.sub.7)(CH.sub.2).sub.2                                           O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.2CH(O-i-C.sub.3 H.sub.7)(CH.sub.2).sub.2                                        O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.2CH(O-t-C.sub.4 H.sub.9)(CH.sub.2).sub.2                                        O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.3CH(SCH.sub.3)CH.sub.2                                                          O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.2CH(SCH.sub.3)(CH.sub.2).sub.2                                                  O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR243##      O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR244##      O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR245##      O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR246##      O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR247##      O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR248##      O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR249##      O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR250##      O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.4CH(OCH.sub.3)                                                                  O  O s-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.3CH(OCH.sub.3)CH.sub.2                                                          O  O s-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  O  O s-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                           O  O s-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.2CH(OC.sub.3 H.sub.7)(CH.sub.2).sub.2                                           O  O s-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.2CH(O-i-C.sub.3 H.sub.7)(CH.sub.2).sub.2                                        O  O s-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.2CH(O-t-C.sub.4 H.sub.9)(CH.sub.2).sub.2                                        O  O s-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.3CH(SCH.sub.3)CH.sub.2                                                          O  O s-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.2CH(SCH.sub.3)(CH.sub.2).sub.2                                                  O  O s-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR251##      O  S i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR252##      O  S i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.4CH(OCH.sub.3)                                                                  O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.3CH(OCH.sub.3)CH.sub.2                                                          O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                           O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.2CH(OC.sub.3 H.sub.7)(CH.sub.2).sub.2                                           O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.2CH(O-i-C.sub.3 H.sub.7)(CH.sub.2).sub.2                                        O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.2CH(O-t-C.sub.4 H.sub.9)(CH.sub.2).sub.2                                        O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.3CH(SCH.sub.3)CH.sub.2                                                          O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.2CH(SCH.sub.3)(CH.sub.2).sub.2                                                  O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR253##      O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR254##      O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR255##      O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR256##      O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR257##      O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR258##      O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR259##      O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR260##      O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.4CH(OCH.sub.3)                                                                  O  O s-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.3CH(OCH.sub.3)CH.sub.2                                                          O  O s-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  O  O s-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                           O  O s-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.2CH(OC.sub.3 H.sub.7)(CH.sub.2).sub.2                                           O  O s-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.2CH(O-i-C.sub.3 H.sub.7)(CH.sub.2).sub.2                                        O  O s-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.2CH(O-t-C.sub.4 H.sub.9)(CH.sub.2).sub.2                                        O  O s-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.3CH(SCH.sub.3)CH.sub.2                                                          O  O s-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H    (CH.sub.2).sub.2CH(SCH.sub.3)(CH.sub.2).sub.2                                                  O  O s-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR261##      O  O s-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR262##      O  O s-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR263##      O  O s-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR264##      O  O s-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR265##      O  O s-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR266##      O  O s-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR267##      O  O s-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                   ##STR268##      O  O s-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                         (CH.sub.2).sub.4CH(OCH.sub.3)                                                                  O  O C.sub.2 H.sub.5                             CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                         (CH.sub.2).sub.3CH(OCH.sub.3)CH.sub.2                                                          O  O C.sub.2 H.sub.5                             CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                         (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  O  O C.sub.2 H.sub.5                             CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                         (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                           O  O C.sub.2 H.sub.5                             CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                         (CH.sub.2).sub.2CH(OC.sub.3 H.sub.7)(CH.sub.2).sub.2                                           O  O C.sub.2 H.sub.5                             CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                         (CH.sub.2).sub.2CH(O-i-C.sub.3 H.sub.7)(CH.sub.2).sub.2                                        O  O C.sub.2 H.sub.5                             CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                         (CH.sub.2).sub.2CH(O-t-C.sub.4 H.sub.9)(CH.sub.2).sub.2                                        O  O C.sub.2 H.sub.5                             CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                         (CH.sub.2).sub.3CH(SCH.sub.3)CH.sub.2                                                          O  O C.sub.2 H.sub.5                             CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                         (CH.sub.2).sub.2CH(SCH.sub.3)(CH.sub.2).sub.2                                                  O  O C.sub.2 H.sub.5                             CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                          ##STR269##      O  O C.sub.2 H.sub.5                             CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                          ##STR270##      O  O C.sub.2 H.sub.5                             CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                          ##STR271##      O  O C.sub.2 H.sub.5                             CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                          ##STR272##      O  O C.sub.2 H.sub.5                             CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                          ##STR273##      O  O C.sub.2 H.sub.5                             CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                          ##STR274##      O  O C.sub.2 H.sub.5                             CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                          ##STR275##      O  O C.sub.2 H.sub.5                             CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                          ##STR276##      O  O C.sub.2 H.sub.5                             CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                         (CH.sub.2).sub.4CH(OCH.sub.3)                                                                  O  O i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                         (CH.sub.2).sub.3CH(OCH.sub.3)CH.sub.2                                                          O  O i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                         (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  O  O i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                         (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                           O  O i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                         (CH.sub.2).sub.2CH(OC.sub.3 H.sub.7)(CH.sub.2).sub.2                                           O  O i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                         (CH.sub.2).sub.2CH(O-i-C.sub.3 H.sub.7)(CH.sub.2).sub.2                                        O  O i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                         (CH.sub.2).sub.2CH(O-t-C.sub.4 H.sub.9)(CH.sub.2).sub.2                                        O  O i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                         (CH.sub.2).sub.3CH(SCH.sub.3)CH.sub.2                                                          O  O i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                         (CH.sub.2).sub.2CH(SCH.sub.3)(CH.sub.2).sub.2                                                  O  O i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                          ##STR277##      O  O i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                          ##STR278##      O  O i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                          ##STR279##      O  O i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                          ##STR280##      O  O i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                          ##STR281##      O  O i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                          ##STR282##      O  O i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                          ##STR283##      O  O i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                          ##STR284##      O  O i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                         (CH.sub.2).sub.4CH(OCH.sub.3)                                                                  O  S i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                         (CH.sub.2).sub.3CH(OCH.sub.3)CH.sub.2                                                          O  S i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                         (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  O  S i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                         (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                           O  S i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                         (CH.sub.2).sub.2CH(OC.sub.3 H.sub.7)(CH.sub.2).sub.2                                           O  S i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                         (CH.sub.2).sub.2CH(O-i-C.sub.3 H.sub.7)(CH.sub.2).sub.2                                        O  S i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                         (CH.sub.2).sub.2CH(O-t-C.sub.4 H.sub.9)(CH.sub.2).sub.2                                        O  S i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                         (CH.sub.2).sub.3CH(SCH.sub.3)CH.sub.2                                                          O  S i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                         (CH.sub.2).sub.2CH(SCH.sub.3)(CH.sub.2).sub.2                                                  O  S i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                          ##STR285##      O  S i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                          ##STR286##      O  S i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                          ##STR287##      O  S i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                          ##STR288##      O  S i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                          ##STR289##      O  S i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                          ##STR290##      O  S i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                          ##STR291##      O  S i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                          ##STR292##      O  S i-C.sub.3 H.sub.7                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                         (CH.sub.2).sub.4CH(OCH.sub.3)                                                                  O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                         (CH.sub.2).sub.3CH(OCH.sub.3)CH.sub.2                                                          O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                         (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                         (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                           O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                         (CH.sub.2).sub.2CH(OC.sub.3 H.sub.7)(CH.sub.2).sub.2                                           O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                         (CH.sub.2).sub.2CH(O-i-C.sub.3 H.sub.7)(CH.sub.2).sub.2                                        O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                         (CH.sub.2).sub.2CH(O-t-C.sub.4 H.sub.9)(CH.sub.2).sub.2                                        O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                         (CH.sub.2).sub.3CH(SCH.sub.3)CH.sub.2                                                          O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                         (CH.sub.2).sub.2CH(SCH.sub.3)(CH.sub.2).sub.2                                                  O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                          ##STR293##      O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                          ##STR294##      O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                          ##STR295##      O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                          ##STR296##      O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                          ##STR297##      O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                          ##STR298##      O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                          ##STR299##      O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                          ##STR300##      O  O i-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                         (CH.sub.2).sub.4CH(OCH.sub.3)                                                                  O  O s-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                         (CH.sub.2).sub.3CH(OCH.sub.3)CH.sub.2                                                          O  O s-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                         (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  O  O s-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                         (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                           O  O s-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                         (CH.sub.2).sub.2CH(OC.sub.3 H.sub.7)(CH.sub.2).sub.2                                           O  O s-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                         (CH.sub.2).sub.2CH(O-i-C.sub.3 H.sub.7)(CH.sub.2).sub.2                                        O  O s-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                         (CH.sub.2).sub.2CH(O-t-C.sub.4 H.sub.9)(CH.sub.2).sub.2                                        O  O s-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                         (CH.sub.2).sub.3CH(SCH.sub.3)CH.sub.2                                                          O  O s-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                         (CH.sub.2).sub.2CH(SCH.sub.3)(CH.sub.2).sub.2                                                  O  O s-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                          ##STR301##      O  O s-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                          ##STR302##      O  O s-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                          ##STR303##      O  O s-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                          ##STR304##      O  O s-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                          ##STR305##      O  O s-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                          ##STR306##      O  O s-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                          ##STR307##      O  O s-C.sub.4 H.sub.9                           CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                          ##STR308##      O  O s-C.sub.4 H.sub.9                           __________________________________________________________________________

The following 3-aryl-4-hydroxy-Δ³ -dihydrofuranone derivatives of theformula (Ig) may be mentioned individually in addition to the compoundsmentioned in the preparation examples:

                                      TABLE 4                                     __________________________________________________________________________     ##STR309##                                                                   X    Y    Z.sub.n                                                                            A    B            E.sup.⊕                                  __________________________________________________________________________    Cl   Cl   H    (CH.sub.2).sub.4CH(OCH.sub.3)                                                                   Na                                           Cl   Cl   H    (CH.sub.2).sub.3CH(OCH.sub.3)CH.sub.2                                                           Na                                           Cl   Cl   H    (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                   Na                                           Cl   Cl   H    (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                            Na                                           Cl   Cl   H    (CH.sub.2).sub.2CH(OC.sub.3 H.sub.7)(CH.sub.2).sub.2                                            Na                                           Cl   Cl   H    (CH.sub.2).sub.2CH(O-i-C.sub.3 H.sub.7)(CH.sub.2).sub.2                                         Na                                           Cl   Cl   H    (CH.sub.2).sub.2CH(O-t-C.sub.4 H.sub.9)(CH.sub.2).sub.2                                         Na                                           Cl   Cl   H    (CH.sub.2).sub.3CH(SCH.sub.3)CH.sub.2                                                           Na                                           Cl   Cl   H    (CH.sub.2).sub.2CH(SCH.sub.3)(CH.sub.2).sub.2                                                   Na                                           Cl   Cl   H                                                                                   ##STR310##       Na                                           Cl   Cl   H                                                                                   ##STR311##       Na                                           Cl   Cl   H                                                                                   ##STR312##       Na                                           Cl   Cl   H                                                                                   ##STR313##       Na                                           Cl   Cl   H                                                                                   ##STR314##       Na                                           Cl   Cl   H                                                                                   ##STR315##       Na                                           Cl   Cl   H                                                                                   ##STR316##       Na                                           Cl   Cl   H                                                                                   ##STR317##       Na                                           Cl   Cl   H    (CH.sub.2).sub.4CH(OCH.sub.3)                                                                   NH.sub.3 -i-C.sub.3 H.sub.7                  Cl   Cl   H    (CH.sub.2).sub.3CH(OCH.sub.3)CH.sub.2                                                           NH.sub.3 -i-C.sub.3 H.sub.7                  Cl   Cl   H    (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                   NH.sub.3 -i-C.sub.3 H.sub.7                  Cl   Cl   H    (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                            NH.sub.3 -i-C.sub.3 H.sub.7                  Cl   Cl   H    (CH.sub.2).sub.2CH(OC.sub.3 H.sub.7)(CH.sub.2).sub.2                                            NH.sub.3 -i-C.sub.3 H.sub.7                  Cl   Cl   H    (CH.sub.2).sub.2CH(O-i-C.sub.3 H.sub.7)(CH.sub.2).sub.2                                         NH.sub.3 -i-C.sub.3 H.sub.7                  Cl   Cl   H    (CH.sub.2).sub.2CH(O-t-C.sub.4 H.sub.9)(CH.sub.2).sub.2                                         NH.sub.3 -i-C.sub.3 H.sub.7                  Cl   Cl   H    (CH.sub.2).sub.3CH(SCH.sub.3)CH.sub.2                                                           NH.sub.3 -i-C.sub.3 H.sub.7                  Cl   Cl   H    (CH.sub.2).sub.2CH(SCH.sub.3)(CH.sub.2).sub.2                                                   NH.sub.3 -i-C.sub.3 H.sub.7                  Cl   Cl   H                                                                                   ##STR318##       NH.sub.3 -i-C.sub.3 H.sub.7                  Cl   Cl   H                                                                                   ##STR319##       NH.sub.3 -i-C.sub.3 H.sub.7                  Cl   Cl   H                                                                                   ##STR320##       NH.sub.3 -i-C.sub.3 H.sub.7                  Cl   Cl   H                                                                                   ##STR321##       NH.sub.3 -i-C.sub.3 H.sub.7                  Cl   Cl   H                                                                                   ##STR322##       NH.sub.3 -i-C.sub.3 H.sub.7                  Cl   Cl   H                                                                                   ##STR323##       NH.sub.3 -i-C.sub.3 H.sub.7                  Cl   Cl   H                                                                                   ##STR324##       NH.sub.3 -i-C.sub.3 H.sub.7                  Cl   Cl   H                                                                                   ##STR325##       NH.sub.3 -i-C.sub.3 H.sub.7                  CH.sub.3                                                                           CH.sub.3                                                                           H    (CH.sub.2).sub.4CH(OCH.sub.3)                                                                   Na                                           CH.sub.3                                                                           CH.sub.3                                                                           H    (CH.sub.2).sub.3CH(OCH.sub.3)CH.sub.2                                                           Na                                           CH.sub.3                                                                           CH.sub.3                                                                           H    (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                   Na                                           CH.sub.3                                                                           CH.sub.3                                                                           H    (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                            Na                                           CH.sub.3                                                                           CH.sub.3                                                                           H    (CH.sub.2).sub.2CH(OC.sub.3 H.sub.7)(CH.sub.2).sub.2                                            Na                                           CH.sub.3                                                                           CH.sub.3                                                                           H    (CH.sub.2).sub.2CH(O-i-C.sub.3 H.sub.7)(CH.sub.2).sub.2                                         Na                                           CH.sub.3                                                                           CH.sub.3                                                                           H    (CH.sub.2).sub.2CH(O-t-C.sub.4 H.sub.9)(CH.sub.2).sub.2                                         Na                                           CH.sub.3                                                                           CH.sub.3                                                                           H    (CH.sub.2).sub.3CH(SCH.sub.3)CH.sub.2                                                           Na                                           CH.sub.3                                                                           CH.sub.3                                                                           H    (CH.sub.2).sub.2CH(SCH.sub.3)(CH.sub.2).sub.2                                                   Na                                           CH.sub.3                                                                           CH.sub.3                                                                           H                                                                                   ##STR326##       Na                                           CH.sub.3                                                                           CH.sub.3                                                                           H                                                                                   ##STR327##       Na                                           CH.sub.3                                                                           CH.sub.3                                                                           H                                                                                   ##STR328##       Na                                           CH.sub.3                                                                           CH.sub.3                                                                           H                                                                                   ##STR329##       Na                                           CH.sub.3                                                                           CH.sub.3                                                                           H                                                                                   ##STR330##       Na                                           CH.sub.3                                                                           CH.sub.3                                                                           H                                                                                   ##STR331##       Na                                           CH.sub.3                                                                           CH.sub.3                                                                           H                                                                                   ##STR332##       Na                                           CH.sub.3                                                                           CH.sub.3                                                                           H                                                                                   ##STR333##       Na                                           CH.sub.3                                                                           CH.sub.3                                                                           H    (CH.sub.2).sub.4CH(OCH.sub.3)                                                                   NH.sub.3 -i-C.sub.3 H.sub.7                  CH.sub.3                                                                           CH.sub.3                                                                           H    (CH.sub.2).sub.3CH(OCH.sub.3)CH.sub.2                                                           NH.sub.3 -i-C.sub.3 H.sub.7                  CH.sub.3                                                                           CH.sub.3                                                                           H    (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                   NH.sub.3 -i-C.sub.3 H.sub.7                  CH.sub.3                                                                           CH.sub.3                                                                           H    (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                            NH.sub.3 -i-C.sub.3 H.sub.7                  CH.sub.3                                                                           CH.sub.3                                                                           H    (CH.sub.2).sub.2CH(OC.sub.3 H.sub.7)(CH.sub.2).sub.2                                            NH.sub.3 -i-C.sub.3 H.sub.7                  CH.sub.3                                                                           CH.sub.3                                                                           H    (CH.sub.2).sub.2CH(O-i-C.sub.3 H.sub.7)(CH.sub.2).sub.2                                         NH.sub.3 -i-C.sub.3 H.sub.7                  CH.sub.3                                                                           CH.sub.3                                                                           H    (CH.sub.2).sub.2CH(O-t-C.sub.4 H.sub.9)(CH.sub.2).sub.2                                         NH.sub.3 -i-C.sub.3 H.sub.7                  CH.sub.3                                                                           CH.sub.3                                                                           H    (CH.sub.2).sub.3CH(SCH.sub.3)CH.sub.2                                                           NH.sub.3 -i-C.sub.3 H.sub.7                  CH.sub.3                                                                           CH.sub.3                                                                           H    (CH.sub.2).sub.2CH(SCH.sub.3)(CH.sub.2).sub.2                                                   NH.sub.3 -i-C.sub.3 H.sub.7                  CH.sub.3                                                                           CH.sub.3                                                                           H                                                                                   ##STR334##       NH.sub.3 -i-C.sub.3 H.sub.7                  CH.sub.3                                                                           CH.sub.3                                                                           H                                                                                   ##STR335##       NH.sub.3 -i-C.sub.3 H.sub.7                  CH.sub.3                                                                           CH.sub.3                                                                           H                                                                                   ##STR336##       NH.sub.3 -i-C.sub.3 H.sub.7                  CH.sub.3                                                                           CH.sub.3                                                                           H                                                                                   ##STR337##       NH.sub.3 -i-C.sub.3 H.sub.7                  CH.sub.3                                                                           CH.sub.3                                                                           H                                                                                   ##STR338##       NH.sub.3 -i-C.sub.3 H.sub.7                  CH.sub.3                                                                           CH.sub.3                                                                           H                                                                                   ##STR339##       NH.sub.3 -i-C.sub.3 H.sub.7                  CH.sub.3                                                                           CH.sub.3                                                                           H                                                                                   ##STR340##       NH.sub.3 -i-C.sub.3 H.sub.7                  CH.sub.3                                                                           CH.sub.3                                                                           H                                                                                   ##STR341##       NH.sub.3 -i-C.sub.3 H.sub.7                  CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                         (CH.sub.2).sub.4CH(OCH.sub.3)                                                                   Na                                           CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                         (CH.sub.2).sub.3CH(OCH.sub.3)CH.sub.2                                                           Na                                           CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                         (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                   Na                                           CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                         (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                            Na                                           CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                         (CH.sub.2).sub.2CH(OC.sub.3 H.sub.7)(CH.sub.2).sub.2                                            Na                                           CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                         (CH.sub.2).sub.2CH(O-i-C.sub.3 H.sub.7)(CH.sub.2).sub.2                                         Na                                           CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                         (CH.sub.2).sub.2CH(O-t-C.sub.4 H.sub.9)(CH.sub.2).sub.2                                         Na                                           CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                         (CH.sub.2).sub.3CH(SCH.sub.3)CH.sub.2                                                           Na                                           CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                         (CH.sub.2).sub.2CH(SCH.sub.3)(CH.sub.2).sub.2                                                   Na                                           CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                          ##STR342##       Na                                           CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                          ##STR343##       Na                                           CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                          ##STR344##       Na                                           CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                          ##STR345##       Na                                           CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                          ##STR346##       Na                                           CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                          ##STR347##       Na                                           CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                          ##STR348##       Na                                           CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                          ##STR349##       Na                                           CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                         (CH.sub.2).sub.4CH(OCH.sub.3)                                                                   NH.sub.3 -i-C.sub.3 H.sub.7                  CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                         (CH.sub.2).sub.3CH(OCH.sub.3)CH.sub.2                                                           NH.sub.3 -i-C.sub.3 H.sub.7                  CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                         (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                   NH.sub.3 -i-C.sub.3 H.sub.7                  CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                         (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                            NH.sub.3 -i-C.sub.3 H.sub.7                  CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                         (CH.sub.2).sub.2CH(OC.sub.3 H.sub.7)(CH.sub.2).sub.2                                            NH.sub.3 -i-C.sub.3 H.sub.7                  CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                         (CH.sub.2).sub.2CH(O-i-C.sub.3 H.sub.7)(CH.sub.2).sub.2                                         NH.sub.3 -i-C.sub.3 H.sub.7                  CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                         (CH.sub.2).sub.2CH(O-t-C.sub.4 H.sub.9)(CH.sub.2).sub.2                                         NH.sub.3 -i-C.sub.3 H.sub.7                  CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                         (CH.sub.2).sub.3CH(SCH.sub.3)CH.sub.2                                                           NH.sub.3 -i-C.sub.3 H.sub.7                  CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                         (CH.sub.2).sub.2CH(SCH.sub.3)(CH.sub.2).sub.2                                                   NH.sub.3 -i-C.sub.3 H.sub.7                  CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                          ##STR350##       NH.sub.3 -i-C.sub.3 H.sub.7                  CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                          ##STR351##       NH.sub.3 -i-C.sub.3 H.sub.7                  CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                          ##STR352##       NH.sub.3 -i-C.sub.3 H.sub.7                  CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                          ##STR353##       NH.sub.3 -i-C.sub.3 H.sub.7                  CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                          ##STR354##       NH.sub.3 -i-C.sub.3 H.sub.7                  CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                          ##STR355##       NH.sub.3 -i-C.sub.3 H.sub.7                  CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                          ##STR356##       NH.sub.3 -i-C.sub.3 H.sub.7                  CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                          ##STR357##       NH.sub.3 -i-C.sub.3 H.sub.7                  __________________________________________________________________________

If, in accordance with process (A), ethyl1-(2,6-dichlorophenylacetyloxy)4-isopropoxy-cyclohexanecarboxylate isused, the course of the process according to the invention can berepresented by the following equation: ##STR358##

If, in accordance with process (B) (variant α),3-(2,4,6-trimethylphenyl)-4-hydroxy-5,5-(2-ethoxy)pentamethylene-Δ.sup.3-dihydrofuran-2-one and pivaloyl chloride are used as startingsubstances, the course of the reaction according to the invention can berepresented by the following equation: ##STR359##

If, in accordance with process B (variant β),3-(2,4,6-trimethylphenyl)-4-hydroxy-5,5-(2-methoxy)tetramethylene-Δ.sup.3-dihydrofuran-2-one and acetic anhydride are used as starting compounds,the course of the process according to the invention can be representedby the following equation: ##STR360##

If, in accordance with process C,3-(2,4-dichlorophenyl)-4-hydroxy-5,5-(3-propoxy)pentamethylene-Δ.sup.3-dihydrofuran-2-one and ethoxyethyl chloroformate are used as startingcompounds, the course of the process according to the invention can berepresented by the following equation: ##STR361##

If, in accordance with process (D.sub.α),3-(2,4,6-trimethylphenyl)-3-hydroxy-5,5-(3-tert-butoxy)pentamethylene-.DELTA.³-dihydrofuran-2-one and methyl chloromonothioformate are used asstarting materials, the course of the reaction can be represented asfollows: ##STR362##

If, in accordance with process (E),3-(2,4,6-trimethylphenyl-4-hydroxy-5,5-(1,2-tetramethylene)trimethylene-.DELTA.³-dihydrofuran-2-one and methanesulphonyl chloride are used as startingmaterials, the course of the reaction can be represented by thefollowing equation: ##STR363##

If, in accordance with process (F),3-(2,4,6-trimethylphenyl-4-hydroxy-5,5-(1,4-oxy)pentamethylene-Δ.sup.3-dihydrofuran-2-one and 2,2,2-trifluoroethylmethanechlorothiophosphonate are used as starting materials, the courseof the reaction can be represented by the following equation: ##STR364##

If, in accordance with process (G.sub.α)3-(2,4,6-trimethylphenyl)-4-hydroxy-5,5-(2,3-tetramethylene)tetramethylene-Δ³-dihydrofuran-2-one and ethyl isocyanate are used as starting materials,the course of the reaction can be represented by the following equation:##STR365##

If, in accordance with process (G.sub.β)3-(2,4,6-trimethylphenyl)-4-hydroxy-5,5-(2-methylmercapto)pentamethylene-.DELTA.³-dihydrofuran-2-one and dimethylcarbamoyl chloride are used as startingmaterials, the course of the reaction can be represented by thefollowing equation: ##STR366##

If, in accordance with process (H),3-(2,4,6-trimethylphenyl)-4-hydroxy-5,5-(2-methoxy)pentamethylene-Δ.sup.3-dihydrofuran-2-one and NaOH are used as reactants, the course of theprocess according to the invention can be represented by the followingequation: ##STR367##

The compounds of the formula (II) ##STR368## in which A, B, X, Y, Z, nand R⁸ have the abovementioned meaning and which are required asstarting substances in the above process (A) are new, but can beprepared in a simple manner by processes known in principle. Forexample, O-acyl-α-hydroxy carboxylic esters of the formula (II) areobtained when

a) 2-hydroxy carboxylic acid (esters) of the formula (XIII) ##STR369##in which R¹² represents hydrogen (XIIIa) or alkyl (XIIIb) and

A and B have the abovementioned meaning,

are acylated with phenylacetyl halides of the formula (XIV) ##STR370##in which X, Y, Z and n have the abovementioned meaning and

Hal represents chlorine or bromine (Chem. Reviews 52 237-416 (1953));

and optionally esterified, or when hydroxy carboxylic acids of theformula (IIa) ##STR371## in which A, B, X, Y, Z and n have theabovementioned meaning

are esterified (Chem. Ind. (London) 1568 (1968).

Compounds of the formula (IIa) can be obtained, for example, from thephenylacetyl halides of the formula (XIII) and hydroxy carboxylic acidsof the formula (XIIIa) (Chem. Reviews 52 237-416 (1953)).

The following compounds of the formula (II) may be mentioned by way ofexample:

Ethyl 1-(2,4-dichlorophenyl-acetyloxy)-2-methoxy-cyclohexanecarboxylate

Ethyl 1-(2,6-dichlorophenyl-acetyloxy)-2-methoxy-cyclohexanecarboxylate

Ethyl1-(2-chloro-6-fluorophenyl-acetyloxy)-2-methoxy-cyclohexanecarboxylate

Ethyl 1-(2,4-dimethylphenyl-acetyloxy)-2-methoxy-cyclohexanecarboxylate

Ethyl 1-(2,6-dimethylphenyl-acetyloxy)-2-methoxy-cyclohexanecarboxylate

Ethyl 1-(2,4,6-trimethylphenyl-acetoxy)-2-methoxycyclohexanecarboxylate

Ethyl1-(2,6-dichloro-4-trifluoromethylphenyl-acetoxy)-2-methoxy-cyclohexanecarboxylate

Ethyl 1-(2,4-dichlorophenyl-acetyloxy)-3-methoxy-cyclohexanecarboxylate

Ethyl 1-(2,6-dichlorophenyl-acetyloxy)-3-methoxy-cyclohexanecarboxylate

Ethyl1-(2-chloro-6-fluorophenyl-acetyloxy)-3-methoxy-cyclohexanecarboxylate

Ethyl 1-(2,4-dimethylphenyl-acetyloxy)-3-methoxy-cyclohexanecarboxylate

Ethyl 1-(2,6-dimethylphenyl-acetyloxy)-3-methoxy-cyclohexanecarboxylate

Ethyl 1-(2,4,6-trimethylphenyl-acetoxy)-3-methoxy-cyclohexanecarboxylate

Ethyl1-(2,6-dichloro-4-trifluoromethylphenyl-acetoxy)-3-methoxy-cyclohexanecarboxylate

Ethyl 1-(2,4-dichlorophenyl-acetyloxy)-4-methoxy-cyclohexanecarboxylate

Ethyl 1-(2,6-dichlorophenyl-acetyloxy)-4-methoxy-cyclohexanecarboxylate

Ethyl1-(2-chloro-6-fluorophenyl-acetyloxy)-4-methoxy-cyclohexanecarboxylate

Ethyl 1-(2,4-dimethylphenyl-acetyloxy)-4-methoxy-cyclohexanecarboxylate

Ethyl 1-(2,6-dimethylphenyl-acetyloxy)-4-methoxy-cyclohexanecarboxylate

Ethyl 1-(2,4,6-trimethylphenyl-acetoxy)-4-methoxy-cyclohexanecarboxylate

Ethyl1-(2,6-dichloro-4-trifluoromethylphenyl-acetoxy)-4-methoxy-cyclohexanecarboxylate

Ethyl 1-(2,4-dichlorophenyl-acetyloxy)-4-ethoxy-cyclohexanecarboxylate

Ethyl 1-(2,6-dichlorophenyl-acetyloxy)-4-ethoxy-cyclohexanecarboxylate

Ethyl1-(2-chloro-6-fluorophenyl-acetyloxy)-4-ethoxy-cyclohexanecarboxylate

Ethyl 1-(2,4-dimethylphenyl-acetyloxy)-4-ethoxy-cyclohexanecarboxylate

Ethyl 1-(2,6-dimethylphenyl-acetyloxy)-4-ethoxy-cyclohexanecarboxylate

Ethyl 1-(2,4,6-trimethylphenyl-acetoxy)-4-ethoxy-cyclohexanecarboxylate

Ethyl1-(2,6-dichloro-4-trifluoromethylphenyl-acetoxy)-4-ethoxy-cyclohexanecarboxylate

Ethyl1-(2,4-dichlorophenyl-acetyloxy)-4-isopropoxy-cyclohexanecarboxylate

Ethyl1-(2,6-dichlorophenyl-acetyloxy)-4-isopropoxy-cyclohexanecarboxylate

Ethyl1-(2-chloro-6-fluorophenyl-acetyloxy)-4-isopropoxy-cyclohexanecarboxylate

Ethyl1-(2,4-dimethylphenyl-acetyloxy)-4-isopropoxy-cyclohexanecarboxylate

Ethyl1-(2,6-dimethylphenyl-acetyloxy)-4-isopropoxy-cyclohexanecarboxylate

Ethyl1-(2,4,6-trimethylphenyl-acetoxy)-4-isopropoxy-cyclohexanecarboxylate

Ethyl1-(2,6-dichloro-4-trifluoromethylphenyl-acetoxy)-4-isopropoxy-cyclohexanecarboxylate

Ethyl 1-(2,4-dichlorophenyl-acetyloxy)-4-t-butoxy-cyclohexanecarboxylate

Ethyl 1-(2,6-dichlorophenyl-acetyloxy)-4-t-butoxy-cyclohexanecarboxylate

Ethyl1-(2-chloro-6-fluorophenyl-acetyloxy)-4-t-butoxy-cyclohexanecarboxylate

Ethyl 1-(2,4-dimethylphenyl-acetyloxy)-4-t-butoxy-cyclohexanecarboxylate

Ethyl 1-(2,6-dimethylphenyl-acetyloxy)-4-t-butoxy-cyclohexanecarboxylate

Ethyl1-(2,4,6-trimethylphenyl-acetoxy)-4-t-butoxy-cyclohexanecarboxylate

Ethyl1-(2,6-dichloro-4-trifluoromethylphenyl-acetoxy)-4-t-butoxy-cyclohexanecarboxylate

Ethyl1-(2,4-dichlorophenyl-acetyloxy)-3,4-trimethylene-cyclohexanecarboxylate

Ethyl1-(2,6-dichlorophenyl-acetyloxy)-3,4-trimethylene-cyclohexanecarboxylate

Ethyl1-(2-chloro-6-fluorophenyl-acetyloxy)-3,4-trimethylene-cyclohexanecarboxylate

Ethyl1-(2,4-dimethylphenyl-acetyloxy)-3,4-trimethylene-cyclohexanecarboxylate

Ethyl1-(2,6-dimethylphenyl-acetyloxy)-3,4-trimethylene-cyclohexanecarboxylate

Ethyl1-(2,4,6-trimethylphenyl-acetoxy)-3,4-trimethylene-cyclohexanecarboxylate

Ethyl1-(2,6-dichloro-4-trifluoromethylphenyl-acetoxy)-3,4-trimethylene-cyclohexanecarboxylate

Ethyl1-(2,4-dichlorophenyl-acetyloxy)-2,5-methylene-cyclohexanecarboxylate

Ethyl1-(2,6-dichlorophenyl-acetyloxy)-2,5-methylene-cyclohexanecarboxylate

Ethyl1-(2-chloro-6-fluorophenyl-acetyloxy)-2,5-methylene-cyclohexanecarboxylate

Ethyl1-(2,4-dimethylphenyl-acetyloxy)-2,5-methylene-cyclohexanecarboxylate

Ethyl1-(2,6-dimethylphenyl-acetyloxy)-2,5-methylene-cyclohexanecarboxylate

Ethyl1-(2,4,6-trimethylphenyl-acetoxy)-2,5-methylene-cyclohexanecarboxylate

Ethyl1-(2,6-dichloro-4-trifluoromethylphenyl-acetoxy)-2,5-methylene-cyclohexanecarboxylate

Process (A) is characterized in that compounds of the formula (II) inwhich A, B, X, Y, Z, n and R⁸ have the abovementioned meaning aresubjected to an intramolecular condensation reaction in the presence ofbases.

Diluents which can be employed in process (A) according to the inventionare all inert organic solvents. The following can preferably be used:hydrocarbons, such as toluene and xylene, furthermore ethers, such asdibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether anddiglycol dimethyl ether, moreover polar solvents, such as dimethylsulphoxide, sulpholane, dimethylformamide and N-methyl-pyrrolidone.Alcohols, such as methanol, ethanol, propanol, iso-propanol, butanol,iso-butanol or tert-butanol, can furthermore be employed.

Bases (deprotonating agents) which can be employed when carrying out theprocess (A) according to the invention are all customary protonacceptors. The following can preferably be used: alkali metal oxides,alkali metal hydroxides, alkali metal carbonates, alkaline earth metaloxides, alkaline earth metal hydroxides and alkaline earth metalcarbonates, such as sodium hydroxide, potassium hydroxide, magnesiumoxide, calcium oxide, sodium carbonate, potassium carbonate and calciumcarbonate, all of which can be used in the presence of phase transfercatalysts, such as, for example, triethylbenzylammonium chloride,tetrabutylammonium bromide, Adogen 464 or TDA 1. Alkali metals, such assodium or potassium, can furthermore be used. Other substances which canbe employed are alkali metal amides, alkali metal hydrides, alkalineearth metal amides and alkaline earth metal hydrides, such as sodiumamide, sodium hydride and calcium hydride, and furthermore also alkalimetal alcoholates, such as sodium methylate, sodium ethylate andpotassium tert-butylate.

When carrying out process (A) according to the invention, the reactiontemperatures can be varied within a substantial range. In general, theprocess is carried out at temperatures between 0° C. and 250° C.,preferably between 50° C. and 150° C.

Process (A) according to the invention is generally carried out underatmospheric pressure.

When carrying out process (A) according to the invention, the reactantsof the formula (II) and the deprotonating bases are generally employedin approximately equimolar amounts. However, it is also possible to useone or the other components in a larger excess (up to 3 mol).

Process (Bα) is characterized in that compounds of the formula (Ia) arereacted with carbonyl halides of the formula (III).

If the acid halides are used, then diluents which can be employed in theprocess (Bα) according to the invention are all solvents which are inertto these compounds. The following can preferably be used: hydrocarbons,such as benzine, benzene, toluene, xylene and tetralin, furthermore,halogenohydrocarbons, such as methylene chloride, chloroform, carbontetrachloride, chlorobenzene and o-dichlorobenzene, furthermore ketones,such as acetone and methyl isopropyl ketone, moreover ethers, such asdiethyl ether, tetrahydrofuran and dioxane, in addition carboxylates,such as ethyl acetate, and also strongly polar solvents, such asdimethyl sulphoxide and sulpholane. If the acid halide is sufficientlystable to hydrolysis, the reaction can also be carried out in thepresence of water.

If the corresponding carbonyl halides are used, then suitableacid-binding agents in the reaction in accordance with process (Bα)according to the invention are all customary acid acceptors. Thefollowing can preferably be used: tertiary amines, such astriethylamine, pyridine, diazabicyclooctane (DABCO),diazabicycloundecane (DBU), diazabicyclononene (DBN), Hunig base andN,N-dimethylaniline, furthermore alkaline earth metal oxides, such asmagnesium oxide and calcium oxide, moreover alkali metal carbonates andalkaline earth metal carbonates, such as sodium carbonate, potassiumcarbonate and calcium carbonate.

When carrying out the process (Bα) according to the invention andcarbonyl halides are used, the reaction temperatures can also be variedwithin a substantial range. In general, the process is carried out attemperatures between -20° C. and +150° C., preferably between 0° C. and100° C.

When carrying out the process (Bα) according to the invention, thestarting substances of the formula (Ia) and the carbonyl halide of theformula (III) are generally used in approximately equivalent amounts.However, it is also possible to employ the carbonyl halide in a largerexcess (up to 5 mol). Working-up is carried out by customary methods.

Process (Bβ) is characterized in that compounds of the formula (Ia) arereacted with carboxylic anhydrides of the formula (IV).

If, in process (Bβ) according to the invention, carboxylic anhydridesare used as reactants of the formula (IV), then suitable diluents whichcan be used are preferably those which are also preferably suitable whenacid halides are used. An excess of the carboxylic anhydride employedcan, furthermore, also act simultaneously as diluent.

When carrying out the process (Bβ) according to the invention andcarboxylic anhydrides are used, the reaction temperatures can be variedwithin a substantial range. In general, the process is carried out attemperatures between -20 C. and +150° C., preferably between 0° C. and100° C.

When carrying out the process (Bβ) according to the invention, thestarting substances of the formula (Ia) and the carboxylic anhydride ofthe formula (IV) are generally used in approximately equivalent amounts.However, it is also possible to employ the carboxylic anhydride in alarger excess (up to 5 mol). Working-up is carried out by customarymethods.

In general, a procedure is followed in which diluent and an excess ofcarboxylic anhydride and also the carboxylic acid which forms areremoved by distillation or by washing with an organic solvent or withwater.

Process (C) is characterized in that compounds of the formula (Ia) arereacted with chloroformic esters or chloroformic thioesters of theformula (V).

If the corresponding chloroformic esters or chloroformic thioesters areused, then suitable acid acceptors in the reaction in accordance withprocess (C) according to the invention are all customary acid acceptors.The following can preferably be used: tertiary amines, such astriethylamine, pyridine, DABCO, DBC, DBA, Hunig base andN,N-dimethyl-aniline, furthermore alkaline earth metal oxides, such asmagnesium oxide and calcium oxide, and moreover alkali metal carbonatesand alkaline earth metal carbonates, such as sodium carbonate, potassiumcarbonate and calcium carbonate.

Diluents which can be employed in process (C) according to the inventionwhen the chloroformic esters or chloroformic thioesters are used are allsolvents which are inert towards these compounds. The following canpreferably be used: hydrocarbons, such as benzine, benzene, toluene,xylene and tetralin, furthermore halogenohydrocarbons, such as methylenechloride, chloroform, carbon tetrachloride, chlorobenzene ando-dichlorobenzene, moreover ketones, such as acetone and methylisopropyl ketone, in addition ethers, such as diethyl ether,tetrahydrofuran and dioxane, additionally carboxylates, such as ethylacetate, and also strongly polar solvents, such as dimethyl sulphoxideand sulpholane.

When using the chloroformic esters or chloroformic thioesters ascarboxylic acid derivatives of the formula (V), the reactiontemperatures, when carrying out process (C) according to the invention,can be varied within a substantial range. If the process is carried outin the presence of a diluent and of an acid-binding agent, the reactiontemperatures are generally between -20° C. and +100° C., preferablybetween 0° C. and 50° C.

Process (C) according to the invention is generally carried out underatmospheric pressure.

For carrying out the process (C) according to the invention, thestarting substances of the formula (Ia) and the particular chloroformicester or chloroformic thioester of the formula (V) are generally used inapproximately equivalent amounts. However, it is also possible to employone or the other components in a larger excess (up to 2 mol). Working-upis then carried out by customary methods. In general, a procedure isfollowed in which precipitated salts are removed and the reactionmixture which remains is concentrated by stripping off the diluent.

In preparation process D, approximately 1 mol of chloromonothioformicester or chlorodithioformic ester of the formula (VI) is employed permol of starting compound of the formula (Ia) at 0° to 120° C.,preferably at 20° to 60° C.

Suitable diluents which may be added are all inert polar organicsolvents, such as ethers, amides, alcohols, sulphones or sulphoxides.

Dimethyl sulphoxide, tetrahydrofuran, dimethylformamide and dimethylsulphide are preferably employed.

If, in a preferred embodiment, the enolate salt of the compound Ia isprepared by adding strong deprotonating agents, such as, for example,sodium hydride or potassium tertiary butylate, a further addition ofacid-binding agents can be dispensed with.

If acid-binding agents are employed, then suitable substances arecustomary inorganic or organic bases; sodium hydroxide, sodiumcarbonate, potassium carbonate, pyridine and triethylamine may bementioned by way of example.

The reaction can be carried out under atmospheric pressure or underelevated pressure, it is preferably carried out under atmosphericpressure. Working-up is carried out by customary methods.

In preparation process (E), approximately 1 mol of sulphonyl chloride(VII) is reacted per mol of starting compound of the formula (Ia) at 0°to 150° C., preferably at 20° to 70° C.

Suitable diluents which may be added are all inert polar organicsolvents, such as ethers, amides, nitriles, alcohols, sulphones andsulphoxides.

Dimethyl sulphoxide, tetrahydrofuran, dimethylformamide and dimethylsulphide are preferably employed.

If, in a preferred embodiment, the enolate salt of the compound Ia issynthesized by adding strong deprotonating agents, (such as, forexample, sodium hydride or potassium tertiary burylate), a furtheraddition of acid-binding agents can be dispensed with.

If acid-binding agents are employed, then suitable substances arecustomary inorganic or organic bases; sodium hydroxide, sodiumcarbonate, potassium carbonate and pyridine may be mentioned by way ofexample.

The reaction can be carried out under atmospheric pressure or underelevated pressure, it is preferably carried out under atmosphericpressure. Working-up is carried out by customary methods.

To obtain compounds of the structure (Ie), in preparation process (F), 1to 2, preferably 1 to 1.3, mol of the phosphorus compound of the formula(VIII) are employed per mol of the compound (Ia) at temperatures between-40° C. and 150° C., preferably between -10° and 110° C.

Suitable diluents which may be added are all inert, polar organicsolvents, such as ethers, amides, nitriles, alcohols, sulphides,sulphones, sulphoxides and the like.

Acetonitrile, dimethyl sulphoxide, tetrahydrofuran, dimethylformamideand dimethyl sulphide are preferably employed.

Suitable acid-binding agents which may be added are customary inorganicor organic bases, such as hydroxides or carbonates. Examples which maybe mentioned are sodium hydroxide, sodium carbonate, potassium carbonateand pyridine.

The reaction can be carried out under atmospheric pressure or underelevated pressure, it is preferably carried out under atmosphericpressure. Working-up is carried out by customary methods of organicchemistry. The end products obtained are preferably purified bycrystallization, chromatography or by so-called "incipientdistillation", i.e. removal of the volatile components in vacuo.

In preparation process G.sub.α, approximately 1 mol of isocyanate of theformula (IX) is reacted per mol of starting compound of the formula Iaat 0° to 100° C., preferably at 20° to 50° C.

Suitable diluents which may be added are all inert organic solvents,such as ethers, amides, nitriles, sulphones and sulphoxides.

If appropriate, catalysts can be added to accelerate the reaction.Catalysts which can be employed very advantageously are organotincompounds, such as, for example, dibutyltin dilaurate. The process ispreferably carried out under atmospheric pressure.

In preparation process G.sub.β, approximately 1 mol of carbamoylchloride or thiocarbamoyl chloride of the formula (X) is reacted per molof starting compound of the formula (Ia) at 0° to 150° C., preferably at20° to 70° C.

Suitable diluents which may be added are all inert polar organicsolvents, such as ethers, amides, alcohols, sulphones and sulphoxides,sulphides.

Dimethyl sulphoxide, tetrahydrofuran, dimethylformamide and dimethylsulphide are preferably employed.

If, in a preferred embodiment, the enolate salt of the compound Ia isprepared by adding strong deprotonating agents (such as, for example,sodium hydride or potassium tertiary butylate), a further addition ofacid-binding agents can be dispensed with.

If acid-binding agents are employed, then suitable substances arecustomary inorganic or organic bases; sodium hydroxide, sodiumcarbonate, potassium carbonate and pyridine may be mentioned by way ofexample.

The reaction can be carried out under atmospheric pressure or underelevated pressure, it is preferably carried out under atmosphericpressure. Working-up is carried out by customary methods.

Process (H) is characterized in that compounds of the formula (Ia) arereacted with metal hydroxides (XI) or amines (XII).

Diluents which can be employed in the process according to the inventionare preferably ethers, such as tetrahydrofuran, dioxane, diethyl ether,or else alcohols, such as methanol, ethanol or isopropanol, but alsowater. Process (H) according to the invention is generally carried outunder atmospheric pressure. The reaction temperatures are generallybetween -20° C. and 100° C., preferably between 0° C. and 50° C.

When carrying out the process (H) according to the invention, thestarting substances of the formula (Ia) and (XII) or (XIII) aregenerally used in approximately equimolar amounts. However, it is alsopossible to employ one or the other component in a larger excess (up to2 mol). In general, a procedure is followed in which the reactionmixture is concentrated by stripping off the diluent.

The compounds of the formula I according to the invention can beemployed for combating pests. Pests are undesired animal pests, inparticular insects, mites and nematodes, which are harmful to plants orhigher animals. However, the pests also include undesired plants.

The active compounds according to the invention are suitable forcombating animal pests, preferably arthropods, in particular insects,arachnida and nematodes, encountered in agriculture, in forestry, in theprotection of stored products and of materials, and in the hygienefield, and have good plant tolerance and favourable toxicity towarm-blooded animals. They are active against normally sensitive andresistant species and against all or some stages of development. Theabovementioned pests include:

From the order of the Isopoda, for example, Oniscus asellus,Armadillidium vulgare and Porcellio scaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Chilopoda, for example, Geophilus carpophagus andScutigera spec.

From the order of the Symphyla, for example, Scutigerella immaculata.

From the order of the Thysanura, for example, Lepisma saccharina.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Orthoptera, for example, Blatta orientalis,Periplaneta americana, Leucophaea maderae, Blattella germanica, Achetadomesticus, Gryllotalpa spp., Locusta migratoria migratorioides,Melanoplus differentialis and Schistocerca gregaria.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Reticulitermes spp.

From the order of the Anoplura, for example, Phylloxera vastatrix,Pemphigus spp., Pediculus humanus corporis, Haematopinus spp. andLinognathus spp.

From the order of the Mallophaga, for example, Trichodectes spp. andDamalinea spp.

From the order of the Thysanoptera, for example, Hercinothrips femoralisand Thrips tabaci.

From the order of the Heteroptera, for example, Eurygaster spp.,Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodniusprolixus and Triatoma spp.

From the order of the Homoptera, for example, Aleurodes brassicae,Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicorynebrassicae, Cryptomyzus ribis, Aphis fabae, Doralis pomi, Eriosomalanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp.,Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus,Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphaxstriatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotushederae, Pseudococcus spp. and Psylla spp.

From the order of the Lepidoptera, for example, Pectinophoragossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletisblancardella, Hyponomeuta padella, Plutella maculipennis, Malacosomaneustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrixthurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltiaspp., Earias insulana, Heliothis spp., Spodoptera exigua, Mamestrabrassicae Panolis flammea, Prodenia litura, Spodoptera spp.,Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyraustanubilalis, Ephestia kuehniella, Galleria mellonella, Tineolabisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoeciapodana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella,Homona magnanima and Tortrix viridana.

From the order of the Coleoptera, for example, Anobium punctatum,Rhizopertha dominica, Acanthoscelides obtectus, Hylotrupes bajulus,Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae,Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis,Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilusspp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchusassimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenusspp., Attagenus spp., Lyctus Spp., Meligethes aeneus, Ptinus spp.,Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor,Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallonsolstitialis and Costelytra zealandica.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampaspp., Lasius spp., Monomorium pharaonis and Vespa spp.

From the order of the Diptera, for example, Aedes spp., Anopheles spp.,Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphoraerythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp.,Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp.,Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinellafrit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleaeand Tipula paludosa.

From the order of the Siphonaptera, for example, Xeno-psylla cheopis andCeratophyllus spp.

From the order of the Arachnida, for example, Scorpio maurus andLatrodectus mactans.

From the order of the Acarina, for example, Acarus siro, Argas spp.,Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, phyllocoptrutaoleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalommaspp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp.,Tarsonemus spp., Bryobia praetiosa, Panonychus spp. and Tetranychus spp.

The plant-parasitic nematodes include Pratylenchus spp., Radopholussimilis, Ditylenchus dipsaci, tylenchulus semipenetrans, Heteroderaspp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinemaspp. and Trichodorus spp.

Besides, the active compounds of the formula (I) according to theinvention also have a good fungicidal activity and can be used forcombating plant diseases, such as, for example, against the pathogencausing rice blast disease (Pyricularia oryzae).

For use as insecticides, acaricides and nematicides, the activecompounds according to the invention can be present in theircommercially available formulations and in the use forms, prepared fromthese formulations, as a mixture with other active compounds, such asinsecticides, attractants, sterilizing agents, acaricides, nematicides,fungicides, growth-regulating substances or herbicides. The insecticidesinclude, for example, phosphates, carbamates, carboxylates, chlorinatedhydrocarbons, phenylureas and substances produced by microorganisms,inter alia.

The active compounds according to the invention can furthermore bepresent in their commercially available formulations and in the useforms, prepared from these formulations, as a mixture with synergisticagents. Synergistic agents are compounds which increase the action ofthe active compounds, without it being necessary for the synergisticagent added to be active itself.

The active compound content of the use forms prepared from thecommercially available formulations can vary within wide limits. Theactive compound concentration of the use forms can be between 0.0000001and 95% by weight of active compound, preferably between 0.0001 and 1%by weight.

They are used in a customary manner suitable for the use form.

The compounds according to the invention are also specially suitable forthe treatment of vegetative and generative propagation material, suchas, for example, seeds of cereals, maize, vegetables and the like, orbulbs, cuttings and the like.

When used against hygiene pests and stored-product pests, the activecompounds are distinguished by an outstanding residual action on woodand clay and by good stability to alkali on limed substrates.

The active compounds according to the invention can also be used asherbicides, preferably as defoliants, desiccants, agents for destroyingbroad-leaved plants and, especially, as weedkillers. By weeds, in thebroadest sense, there are to be understood all plants which grow inlocations where they are undesired. Whether the substances according tothe invention act as total or selective herbicides depends essentiallyon the amount used.

The active compounds according to the invention can be used, forexample, in connection with the following plants:

Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria,Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio,Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum,Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala,Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis,Papaver, Centaurea, Trifolium, Ranunculus and Taraxacum.

Dicotyledon cultures of the genera: Gossypium, Glycine, Beta, Daucus,Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana,Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.

Monocotyledon weeds of the qenera: Echinochloa, Setaria, Panicum,Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus,Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis,Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea,Dactyloctenium, Agrostis, Alopecurus and Apera.

Monocotyledon cultures of the genera: Oryza, Zea, Triticum, Hordeum,Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus andAllium.

However, the use of the active compounds according to the invention isin no way restricted to these genera, but also extends in the samemanner to other plants.

The compounds are suitable, depending on the concentration, for thetotal combating of weeds, for example on industrial terrain and railtracks, and on paths and squares with or without tree plantings.Equally, the compounds can be employed for combating weeds in perennialcultures, for example afforestations,decorative tree plantings,orchards, vineyards, citrus groves, nut orchards, banana plantations,coffee plantations, tea plantations, rubber plantations, oil palmplantations, cocoa plantations, soft fruit plantings and hopfields, inlawns, turf and pasture-land, and for the selective combating of weedsin annual cultures.

The compounds of the formula (I) according to the invention areparticularly suitable for selectively combating monocotyledon weeds indicotyledon cultures, by the pre- and also the post-emergence method.

For combating weeds, the active compounds according to the invention, assuch or in the form of their formulations, can also be used as mixtureswith known herbicides, finished formulations or tank mixes beingpossible.

Suitable herbicides for the mixtures are known herbicides, for exampleanilides such as, for example, diflufenican and propanil; arylcarboxylicacids such as, for example, dichloropicolinic acid, dicamba andpicloram; aryloxyalkanoic acids such as, for example, 2,4 D, 2,4 DB, 2,4DP, fluroxypyr, MCPA, MCPP and triclopyr; aryloxy-phenoxy-alkanoicesters such as, for example, diclofop-methyl, fenoxaprop-ethyl,fluazifop-butyl, butyl, haloxyfop-methyl and quizalofop-ethyl; azinonessuch as, for example, chloridazon and norflurazon; carbamates such as,for example, chlorpropham, desmedipham, phenmedipham and propham;chloroacetanilides such as, for exmaple, alachlor, acetochlor,butachlor, metazachlor, metolachlor, pretilachlor and propachlor;dinitroanilines such as, for example, oryzalin, pendimethalin andtrifluralin; diphenyl ethers such as, for example, acifluorfen, bifenox,fluoroglycofen, fomesafen, halosafen, lactofen and oxyfluorfen; ureassuch as, for example, chlortoluron, diuron, fluometuron, isoproturon,linuron and methabenzthiazuron; hydroxylamines such as, for example,alloxydim, clethodim, cycloxydim, sethoxydim and tralkoxydim;imidazolinones such as, for example, imazethapyr, imazamethabenz,imazapyr and imazaquin; nitriles such as, for example, bromoxynil,dichlobenil and ioxynil; oxyacetamides such as, for example, mefenacet;sulphonylureas such as, for example, amidosulfuron, bensulfuron-methyl,chlorimuron-ethyl, chlorsulfuron, cinosulfuron, metsulfuron-methyl,nicosulfuron, primisulfuron, pyrazosulfuron-ethyl,thifensulfuron-methyl, triasulfuron and tribenuron-methyl;thiocarbamates such as, for example, butylate, cycloate, diallate, EPTC,esprocarb, molinate, prosulfocarb, thiobencarb and tri-allate; triazinessuch as, for example, atrazine, cyanazine, simazine, simetryn, terbutrynand terbutylazine; triazinones such as, for example, hexazinone,metamitron and metribuzin; others such as, for example, aminotriazole,benfuresate, bentazone, cinmethylin, clomazone, clopyralid, difenzoquat,dithiopyr, ethofumesate, fluorochloridone, glufosinate, glyphosate,isoxaben, pyridate, quinchlorac, quinmerac, sulfosate and tridiphane.

Mixtures with other known active compounds, such as fungicides,insecticides, acaricides, nematicides, bird repellants, plant nutrientsand agents which improve soil structure, are also possible.

The following insecticides may be mentioned:

acrinathrin, alphamethrin, betacyfluthrin, bifenthrin, brofenprox,cis-resmethrin, clocythrin, cycloprothrin, cyfluthrin, cyhalothrin,cypermethrin, deltamethrin, esfenvalerate, etofenprox, fenpropathrin,fenvalerate, flucythrinate, fluvalinate, lambda-cyhalothrin, permethrin,pyresmetherin, pyrethrum, silafluofen, tralomethrin, zetamethrin,

alaycarb, bendiocarb, benfuracarb, bufencarb, butocarboxim, carbaryl,cartap, ethiofencarb, fenobucarb, fenoxycarb, isoprocarb, methiocarb,methomyl, metolcarb, oxamyl, pirimicarb, promecarb, propoxur, terbam,thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb,

acephate, azinphos A, azinphos M, bromophos A, cadusafos,carbophenothion, chlorfenvinphos, chlormephos, chlorpyrifos,chlorpyrifos M, cyanophos, demeton M, demeton-S-methyl, demeton S,diazinon, dichlorvos, dicliphos, dichlorfenthion, dicrotophosdimethoate, dimethylvinphos, dioxathion, disulfoton edifenphos, ethion,etrimphos, fenitrothion, fenthion fonophos, formothion, heptonophos,iprobenfos isazophos, isoxathion, phorate, malathion, mecarbammervinphos, mesulfenphos, methacrifos, methamidophos naled, omethoate,oxydemeton M, oxydeprofos, parathion A, parathion M, phenthoate,phorate, phosalone, phosmet, phosphamdon, phoxim, pirimiphos A,pirimiphos M, propaphos, prothiophos, prothoate, pyraclophos,pyridaphenthion, quinalphos, salithion, sebufos, sulfotep, sulprofos,tetrachlorvinphos, temephos, thiomethon, thionazin, trichlorfon,triazophos, vamidothion, DMTP (O,O-dimethyl S5-methoxy-1,3,4-thiadiazol-2(3H)-onyl-(3)-methyl!dithiophosphate), DDVP(dimethyl 2,2-dichlorovinyl phosphate), CYAP (O,O-dimethylO-4-cyanophenyl thiophosphate),

buprofezin, chlorfluazuron, diflubenzron, flucycloxuron, flufenoxuron,hexaflumuron, pyriproxifen, tebufenozide, teflubenzuron, triflumuron,

imidacloprid, nitenpyram, N-(6-chloro-3-pyridinyl)-methyl!-N,-cyano-N-methylethaneimide-amide(NI-25),

abamectin, amitrazin, avermectin, azadirachtin, bensultap, Bacillusthuringiensis, cyromazine, diafenthiuron, emamectin, ethofenprox,fenpyrad, fipronil, flufenprox, lufenuron, metaldehyde, milbemectin,pymetrozine, tebufenpyrad, triazuron, aldicarb, bendiocarb, benfuracarb,carbofuran, carbosulfan, chlorethoxyfos, cloethocarb, disulfoton,ethophophos, etrimphos, fenamiphos, fipronil, fonofos, fosthiazate,furathiocarb, HCH, isazophos, isofenphos, methiocarb, monocrotophos,nitenpyram, oxamyl, phorate, phoxim, prothiofos, pyrachlofos, sebufos,phoxim, prothiofos, pyrachlofos, sebufos, silafluofen, tebupirimphos,tefluthrin, terbufos, thiodicarb, thiafenox,

azocyclotin, butylpyridaben, clofentezine, cyhexatin, difenthiuron,diethion, emamectin, fenazaquin, fenbutatin oxide, fenothiocarb,fenpropathrin, fenpyrad, fenpyroximate, fluazinam, fluazuron,flucycloxuron, flufenoxuron, fluvalinate, fubfenfox, hexythiazox,ivemectin, methidathion, monocrotophos, moxidectin, naled, phosalone,profenofos, pyraclofos, pyridaben, pyrimidifen, tebufenpyrad,thuringiensin, triarathene and also4-bromo-2-(4-chlorophenyl)-1-(ethoxymethyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile(AC 303630),

dicotol, chlorobenzilate, bromopropylate, chlorofenson, BPPS.

Particularly favorable mixing partners are furthermore, for example, thefollowing:

Fungicides:

2-aminobutane; 2-anilino-4-methyl-6-cyclopropyl-pyrimidine;2',6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoro-methyl-1,3-thiazole-5-carboxanilide;2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide;(E)-2-methoxyimino-N-methyl-2-(2-phenoxyphenyl)-acetamide;8-hydroxyquinoline sulfate; methyl (E)-2-{2-6-(2-cyanophenoxy)-pyrimidin-4-yloxy!-phenyl}-3-methoxy-acrylate; methyl(E)-methoximino alpha-(o-tolyloxy)-otolyl!acetate; 2-phenylphenol (OPP,aldimorph, ampropylfos, anilazine, azaconazole, benalaxyl, benodanil,benomyl, binapacryl, biphenyl, bitertanol, blasticidin-S, bromuconazole,bupirimate, buthiobate, calcium polysulfide, captafol, captan,carbendazime, carboxine, chinomethionate (quinomethionate), chloroneb,chloropicrin, chlorothalonil, chlozolinate, cufraneb, cymoxanil,cyproconazole, cyprofuram, dichloropren, diclobutrazole, diclofluanid,diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol,dimethomorph, diniconazole, dinocap, diphenylamine, dipyrithione,ditalimfos, dithianon, dodine,drazoxolon, edifenphos, epoxyconazole,ethirimol, etridiazole, fenamirol, fenbuconazole, fenfuram, fenitropan,fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentinhydroxide, ferbam, ferimzone, fluazinam, fludioxonil, fluoromide,fluquinconazole, flusilazole, flusulfamide, flutolanil, flutriafol,folpet, fosetyl-aluminum, fthalide, fuberidazole, furalaxyl,furmecyclox, guazatine, hexachlorobenzene, hexaconazole, hymexazole,imazalil, imibenconazole, iminoctadin, iprobenfos (IBP), iprodione,isoprothiolan, kasugamycin, copper formulations, such as: copperhydroxide, copper naphthenate, copper oxychloride, copper sulfate,copper dioxide, oxine-copper and Bordeaux mixture, mancopper, mancozeb,maneb, mepanipyrim, mepronil, metalaxyl, metconazole, methasulfocarb,methfuroxam, metiram, metsulfovax, myclobutanil, nickel,dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol, ofurace,oxadixyl, oxamocarb, oxycarboxin, pefurazoate, penconazole, pencycuron,phosdiphen, phthalide, pimaricin, piperalin, polycarbamate, polyoxin,probenazole, prochloraz, procymidon, propamocarb, propioconazole,propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilon, quintozen(PCNB), sulfur and sulfur formulations, tebuconazole, tecloftalam,tecnazen, tetraconazole, thiabendazole, thicyofen, thiophanate-methyl,thiram, tolclophos-methyl, tolylfluanid, triadimefon, triadimenol,triazoxide, trichlamid, tricyclazole, tridemorph, triflumizole,triforin, triticonazole, validamycin A, vinclozolin, zineb, ziram.

Bactericides:

Bronopol, dichlorophen, nitrapyrin, nickel dimethyl-dithiocarbamate,kasugamycin, octhilinon, furancarboxylic acid, oxytetracycline,probenazole, streptomycin, tecloftalam, copper sulfate and other copperformulations.

The active compounds can be used as such, in the form of theirformulations or in the use forms prepared therefrom by further dilution,such as ready-to-use solutions, suspensions, emulsions, powders, pastesand granules. They are used in the customary manner, for example bywatering, spraying, atomizing or scattering.

The active compounds according to the invention can be applied eitherbefore or after emergence of the plants.

They can also be incorporated into the soil before sowing.

The amount of active compound used can vary within a substantial range.It depends essentially on the nature of the desired effect. In general,the amounts used are between 10 g and 10 kg of active compound perhectare of soil surface, preferably between 50 g and 5 kg per ha.

To prepare the pesticides, the active compounds according to theinvention can be converted into the customary formulations, such assolutions, emulsions, suspensions, powders, foams, pastes, granules,aerosols, natural and synthetic materials impregnated with activecompound, and very fine capsules in polymeric substances and in coatingcompositions for seeds, furthermore in formulations used with burningequipment, such as fumigating cartridges, fumigating cans, fumigatingcoils and the like, as well as ULV cold-mist and warm-mist formulations.

Depending on their particular physical and/or chemical properties, theactive compounds can be converted to the customary formulations, such assolutions, emulsions, suspensions, powders, foams, pastes, granules,aerosols, natural and synthetic materials impregnated with activecompound, very fine capsules in polymeric substances and in coatingcompositions for seeds, and furthermore in formulations used withburning equipment, such as fumigating cartridges, fumigating cans,fumigating coils and the like, as well as ULV cold-mist and warm-mistformulations.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is, liquid solvents, liquefiedgases under pressure, and/or solid carriers, optionally with the use ofsurface-active agents, that is, emulsifying agents and/or dispersingagents, and/or foam-forming agents. In the case of the use of water asan extender, organic solvents can, for example, also be used asauxiliary solvents. As liquid solvents, there are suitable in the main:aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinatedaromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes,chloroethylenes or methylene chloride, aliphatic hydrocarbons, such ascyclohexane or paraffins, for example mineral oil fractions, alcohols,such as butanol or glycol as well as their ethers and esters, ketones,such as acetone, methyl ethyl ketone, methyl isobutyl ketone orcyclohexanone, strongly polar solvents, such as dimethylformamide anddimethyl sulphoxide, as well as water; by liquefied gaseous extenders orcarriers are meant liquids which are gaseous at ambient temperature andunder atmospheric pressure, for example aerosol propellants, such ashalogenated hydrocarbons as well as butane, propane, nitrogen and carbondioxide; as solid carriers there are suitable: for example groundnatural minerals, such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals, such as highly-disperse silica, alumina and silicates; assolid carriers for granules there are suitable: for example crushed andfractionated natural rocks such as calcite, marble, pumice, sepioliteand dolomite, as well as synthetic granules of inorganic and organicmeals, and granules of organic material such as sawdust, coconut shells,maize cobs and tobacco stalks; as emulsifying and/or foam-forming agentsthere are suitable: for example non-ionic and anionic emulsifiers, suchas polyoxyethylene fatty acid esters, polyoxyethylene fatty alcoholethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkylsulphates, arylsulphonates as well as albumen hydrolysis products; asdispersing agents there are suitable: for example lignin-sulphite wasteliquors and methylcellulose.

Adhesives such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Other additives can bemineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedyestuffs, and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

The formulations in general contain between 0.1 and 95 per cent byweight of active compound, preferably between 0.5 and 90%.

The active compounds according to the invention can be present in theircommercially available formulations and in the use forms, prepared fromthese formulations, as a mixture with other active compounds, such asinsecticides, attractants, sterilizing agents, acaricides, nematicides,fungicides, growth-regulating substances or herbicides. The insecticidesinclude, for example, phosphates, carbamates, carboxylates, chlorinatedhydrocarbons, phenylureas and substances produced by microorganisms.

The compositions according to the invention preferably contain, besidesat least one of a compound of the general formula (I) and, ifappropriate, besides conventional extenders and auxiliaries, at leastone surface-active substance.

The preparation of the compounds of the general formula (I) according tothe invention will be illustrated by the preparation examples whichfollow, and the biological activity by the biological examples whichfollow.

The compounds listed below will be used as comparison substances in theuse examples which follow: ##STR372## (all disclosed in EP 0,528,156)

EXAMPLE A

Heliothis virescens test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Soybean shoots (Glycine max) are treated by being dipped into thepreparation of active compound of the desired concentration and areinfested with tobacco budwork caterpillars (Heliothis virescens) whilethe leaves are still moist.

After the specified periods of time, the destruction in is determined.100% means that all the caterpillars have been killed; 0% means thatnone of the caterpillars have been killed.

In this test, for example the compounds of Preparation Examples Ib-6,Ib-8, Ic-4 and Ic-5 resulted in a destruction of 100% after 7 days at anexemplary concentration of active compound of 0.1%, while the compoundsof the prior art resulted in a destruction of not more than 40%.

EXAMPLE B

Myzus test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Cabbage leaves (Brassica oleracea) which are heavily infested with thegreen peach aphid (Myzus persicae) are treated by being dipped into thepreparation of active compound of the desired concentration.

After the specified periods of time, the destruction in is determined.100% means that all the aphids have been killed; 0% means that none ofthe aphids have been killed.

In this test, for example the compounds of Preparation Examples Ic-4 andIc-5 show a degree of destruction of not less than 85% after 6 days atan exemplary concentration of active compound of 0.01%.

EXAMPLE C

Critical concentration test/root-systemic action

Test insect: Phaedon cochleariae larvae

Solvent: 4 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

The preparation of active compound is intimately mixed with soil. Theconcentration of the active compound in the preparation is ofpractically no importance, only the amount by weight of active compoundper unit volume of soil, which is given in ppm (=mg/1), being decisive.The treated soil is transferred into pots and these are planted withcabbage (Brassica oleracea). The active compound can in this way betaken up from the soil by the roots of the plants and be transportedinto the leaves.

To demonstrate the root-systemic effect, the leaves are infested withthe abovementioned test animals after 7 days. After a further 2 days,the evaluation is made by counting or estimating the dead animals. Theroot-systemic action of the active compound is deduced from themortality figures. It is 100% if all test animals have been killed and0% if just as many test insects are still alive as in the case of theuntreated control.

In this test, for example the compound of Preparation Example Ic-4 showsa degree of destruction of 100% at an exemplary concentration of activecompound of 20 ppm.

EXAMPLE D

Tetranychus test (OP resistant)

Solvent: 3 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Bean plants (Phaseolus vulgaris) which are heavily infested with alldevelopment stages of the two-spotted spider mite (Tetranychus urticae)are sprayed with a preparation of active compound of the desiredconcentration.

After the specified periods of time, the destruction in is estimated.100% means that all the spider mites have been killed; 0% means thatnone of the spider mites have been killed.

In this test, for example the compound of Preparation Example Ic-5showed a degree of destruction of 100% after 14 days at an exemplaryconcentration of active substance of 0.004%.

EXAMPLE E

Panonychus test

Solvent: 3 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, and theconcentrate is diluted with emulsifier-containing water to the desiredconcentration.

Plum trees (Prunus domestica) approximately 30 cm in height, which areheavily infested with all development stages of the red spider(Panonychus ulmi), are sprayed with a preparation of active compound ofthe desired concentration.

After the specified periods of time, the activity in % is determined.100% means that all the spider mites have been killed; 0% means thatnone of the spider mites have been killed.

In this test, for example the compound of Preparation Example Ic-4showed a degree of destruction of 100% after 14 days at an exemplaryconcentration of active substance of 0.004%.

EXAMPLE F

Pre-emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Seeds of the test plants are sown in normal soil and, after 24 hours,watered with the preparation of the active compound. It is expedient tokeep constant the amount of water per unit area. The concentration ofthe active compound in the preparation is of no importance, only theamount of active compound applied per unit area being decisive. Afterthree weeks, the degree of damage to the plants is rated in % damage incomparison to the development of the untreated control.

The figures denote:

0%=no action (like untreated control)

100%=total destruction

A clearly superior activity and crop plant selectivity compared with theprior art are shown, in this test, for example by the compounds ofPreparation Examples Ia-4, Ib-6, Ib-8, Ic-4 and Ic-5.

EXAMPLE G

Post-emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Test plants which have a height of 5-15 cm are sprayed with thepreparation of the active compound in such a way as to apply theparticular amounts of active compound desired per unit area. Theconcentration of the spray liquor is chosen so that the particularamounts of active compound desired are applied in 2,000 l of water/ha.After three weeks, the degree of damage to the plants is rated in %damage in comparison to the development of the untreated control. Thefigures denote:

0%=no action (like untreated control)

100%=total destruction

A clearly superior activity and crop plant selectivity compared with theprior art are shown, in this test, for example by the compounds ofPreparation Examples Ia-4, Ib-6, Ib-8 and Ic-4.

EXAMPLE Ia-1 ##STR373##

16.83 g (0.15 mol) of potassium tert-butylate are introduced into 100 mlof absolute DMF, a solution of 37.10 g (0.10 mol) of ethyl2-O-(2,4-dichlorophenylacetyl)norbornane-2-carboxylate in 100 ml ofabsolute DMF is added dropwise at 0°-10° C., and the mixture is stirredfor 16 hours at room temperature.

For working-up, the reaction mixture is added dropwise to 500 ml of 1Nhydrochloric acid, and the product which has precipitated is filteredoff with suction and dried in a vacuum drying oven. Yield: 29.79 g (92%of theory) of a white solid of m.p. 227° C.

The compounds described in Table 5 were prepared analogously.

                                      TABLE 5                                     __________________________________________________________________________     ##STR374##                                                                   Ex. No.                                                                           X  Y    Z.sub.n                                                                           A    B           m.p. °C.                              __________________________________________________________________________    Ia-2                                                                              Cl Cl   H   (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  220                                          Ia-3                                                                              CH.sub.3                                                                         CH.sub.3                                                                           H   (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  179                                          Ia-4                                                                              CH.sub.3                                                                         CH.sub.3                                                                           6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  220-222                                      Ia-5                                                                              CH.sub.3                                                                         CH.sub.3                                                                           6-CH.sub.3                                                                         ##STR375##      140-145                                      Ia-6                                                                              CH.sub.3                                                                         CH.sub.3                                                                           6-CH.sub.3                                                                         ##STR376##      204-205                                      Ia-7                                                                              CH.sub.3                                                                         CH.sub.3                                                                           6-CH.sub.3                                                                         ##STR377##      217 (Z)                                      Ia-8                                                                              CH.sub.3                                                                         CH.sub.3                                                                           H                                                                                  ##STR378##      210                                          Ia-9                                                                              CH.sub.3                                                                         CH.sub.3                                                                           6-CH.sub.3                                                                         ##STR379##      >230                                         Ia-4                                                                              CH.sub.3                                                                         CH.sub.3                                                                           6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  187                                          trans                                                                         Ia-4                                                                              CH.sub.3                                                                         CH.sub.3                                                                           6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  >250                                         cis                                                                           Ia-10                                                                             CH.sub.3                                                                         CH.sub.3                                                                           6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                           Oil                                          Ia-11                                                                             Cl Cl   H   (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                           204-210                                      Ia-12                                                                             CH.sub.3                                                                         CH.sub.3                                                                           H   (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                           172-182                                      Ia-13                                                                             CH.sub.3                                                                         CH.sub.3                                                                           6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(O-n-C.sub.3 H.sub.7)(CH.sub.2).sub.2                                        172-175                                      Ia-14                                                                             CH.sub.3                                                                         CH.sub.3                                                                           6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(O-n-C.sub.4 H.sub.9)(CH.sub.2).sub.2                                        Oil                                          Ia-15                                                                             CH.sub.3                                                                         t-C.sub.4 H.sub.9                                                                  H   (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  150-165                                      Ia-16                                                                             CH.sub.3                                                                         t-C.sub.4 H.sub.9                                                                  6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.3).sub.2(CH.sub.2).sub.2                                            206-210                                      Ia-17                                                                             CH.sub.3                                                                         CH.sub.3                                                                           6-CH.sub.3                                                                         ##STR380##      218-220                                      Ia-18                                                                             Cl Cl   H                                                                                  ##STR381##      223                                          Ia-19                                                                             CH.sub.3                                                                         CH.sub.3                                                                           H                                                                                  ##STR382##      240-242                                      Ia-20                                                                             CH.sub.3                                                                         CH.sub.3                                                                           6-CH.sub.3                                                                        CH.sub.2CH(SCH.sub.3)(CH.sub.2).sub.3                                                          245-247                                      Ia-21                                                                             CH.sub.3                                                                         CH.sub.3                                                                           6-CH.sub.3                                                                        CH(OCH.sub.3)(CH.sub.2).sub.4                                                                  Oil                                          Ia-22                                                                             CH.sub.3                                                                         CH.sub.3                                                                           6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(CO.sub.2 C.sub.2 H.sub.5)(CH.sub.2).sub                    .2               165-180                                      Ia-23                                                                             CH.sub.3                                                                         CH.sub.3                                                                           6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(CO.sub.2 H)(CH.sub.2).sub.2                                                 >250                                         __________________________________________________________________________

EXAMPLE Ib-1 ##STR383##

3.25 g (10 mmol) of the compound Ia-1 are introduced into 40 ml ofabsolute methylene chloride, 1.42 g (14 mmol) of triethylamine and aspatula-tip of DMAP were added, a solution of 0.94 g (12 mmol) of acetylchloride in 20 ml of methylene chloride was added drop-wise, and themixture was stirred for 16 hours at room temperature.

For working-up, the reaction mixture is washed using aqueous citricacid, NaHCO₃ solution and NaCl solution, dried and evaporated in arotary evaporator. Further purification is carried out by flashchromatography on silica gel using cyclohexane/ethyl acetate 3:1. Yield:1.70 g (46% of theory) of a solid of m.p. 126° C.

The compounds listed in Table 6 were prepared analogously.

                                      TABLE 6                                     __________________________________________________________________________     ##STR384##                                                                   Ex. No.                                                                            X   Y   Z.sub.n                                                                           A    B           R.sup.1       m.p.. °C.              __________________________________________________________________________    Ib-2 Cl  Cl  H   (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  CH.sub.3      Oil                           Ib-3 Cl  Cl  H   (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                t-C.sub.4 H.sub.9                                                                  Oil                                                                      Ib-4 CH.sub.3                                                                          CH.sub.3                                                                          H   (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  CH.sub.3      Oil                           Ib-5 CH.sub.3                                                                          CH.sub.3                                                                          H   (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                t-C.sub.4 H.sub.9                                                                  134                                                                      Ib-6 CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  CH.sub.3      Oil                           Ib-7 CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                i-C.sub.3 H.sub.7                                                                  Oil                                                                      Ib-8 CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                t-C{hd 4 H.sub.9                                                                   78-80                                                                    Ib-9 CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  C(CH.sub.3).sub.2CH.sub.2 Cl                                                                113-115                       Ib-10                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  CCH.sub.3 (CH.sub.2 Cl).sub.2                                                               118-120                       Ib-11                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  CCH.sub.3 (CH.sub.2 OCH.sub.3).sub.2                                                        103-104                       Ib-12                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                   ##STR385##   106-107                       Ib-13                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  C.sub.2 H.sub.5                                                                             Oil                           Ib-14                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                   ##STR386##   Oil                           Ib-15                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  C(CH.sub.3).sub.2 C.sub.2 H.sub.5                                                           107-108                       Ib-16                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  C(CH.sub.3).sub.2 i-C.sub.3 H.sub.7                                                         94-96                         Ib-17                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                   ##STR387##   Oil                           Ib-18                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                   ##STR388##   Oil                           Ib-19                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                   ##STR389##   200-202                       Ib-20                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  CH.sub.2 -t-C.sub.4 H.sub.9                                                                 126-129                       Ib-21                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  C.sub.6 H.sub.5                                                                             Oil                           Ib-22                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  CHC(CH.sub.3).sub.2                                                                         107-108                       Ib-23                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                   ##STR390##   Oil                           Ib-24                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR391##      t-C.sub.4 H.sub.9                                                                           Oil                           Ib-25                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR392##      CH.sub.3      76-78                         Ib-26                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR393##                                                  i-C.sub.3 H.sub.7                                                                  Oil                                                                      Ib-27                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR394##                                                  t-C.sub.4 H.sub.9                                                                  114-116                                                                  Ib-28                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR395##      CH.sub.3      188-189                       Ib-29                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR396##                                                  t-C.sub.4 H.sub.9                                                                  131                                                                      Ib-30                                                                              Cl  Cl  H                                                                                  ##STR397##                                                  t-C.sub.4 H.sub.9                                                                  112                                                                      Ib-31                                                                              CH.sub.3                                                                          CH.sub.3                                                                          H                                                                                  ##STR398##      CH.sub.3      105                           Ib-32                                                                              CH.sub.3                                                                          CH.sub.3                                                                          H                                                                                  ##STR399##      t-C.sub.4 H.sub.9                                                                           Oil                           Ib-33                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR400##      CH.sub.3      159                           Ib-34                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR401##                                                  i-C.sub.3 H.sub.7                                                                  104                                                                      Ib-35                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR402##                                                  t-C.sub.4 H.sub.9                                                                  102-103                                                                  Ib-36                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR403##      C(CH.sub.3).sub.2CH.sub.2 Cl                                                                111                           Ib-37                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR404##      C(CH.sub.2 Cl).sub.2 CH.sub.3                                                               136                           Ib-38                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR405##      C(CH.sub.2OCH.sub.3).sub.2 CH.sub.3                                                         119                           Ib-39                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR406##      C(CH.sub.3).sub.2C.sub.2 H.sub.5                                                            105                           Ib-40                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR407##      C(CH.sub.3).sub.2 -i-C.sub.3 H.sub.7                                                        138                           Ib-41                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR408##                                                                                     ##STR409##   119                           Ib-43                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  Cl(CH.sub.2).sub.3                                                                          Oil                           Ib-44                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                   ##STR410##   120                           Ib-45                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2)                                                  ##STR411##   Oil                           Ib-46                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                   ##STR412##   Oil                           Ib-47                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                           i-C.sub.3 H.sub.7                                                                           130-134                       Ib-48                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                           t-C.sub.4 H.sub.9                                                                           133-135                       Ib-49                                                                              Cl  Cl  H   (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                           t-C.sub.4 H.sub.9                                                                           Oil                           Ib-50                                                                              CH.sub.3                                                                          CH.sub.3                                                                          H   (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                           t-C.sub.4 H.sub.9                                                                           127                           Ib-51                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OC.sub.3 H.sub.7)(CH.sub.2).sub.2                                           t-C.sub.4 H.sub.9                                                                           127-130                       Ib-52                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OC.sub.4 H.sub.9)(CH.sub.2).sub.2                                           t-C.sub.4 H.sub.9                                                                           140                           Ib-53                                                                              CH.sub.3                                                                          t-C.sub.4 H.sub.9                                                                 H   (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  t-C.sub.4 H.sub.9                                                                           160                           Ib-54                                                                              CH.sub.3                                                                          t-C.sub.4 H.sub.9                                                                 6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  t-C.sub.4 H.sub.9                                                                           188-190                       Ib-55                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR413##      i-C.sub.3 H.sub.7                                                                           114-116                       Ib-56                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR414##      t-C.sub.4 H.sub.9                                                                           116-118                       Ib-57                                                                              Cl  Cl  H                                                                                  ##STR415##      t-C.sub.4 H.sub.9                                                                           123-125                       Ib-58                                                                              CH.sub.3                                                                          CH.sub.3                                                                          H                                                                                  ##STR416##      t-C.sub.4 H.sub.9                                                                           Oil                           Ib-59                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        CH.sub.2CH(SCH.sub.3)(CH.sub.2).sub.3                                                          i-C.sub.3 H.sub.7                                                                           136-137                       Ib-60                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        CH.sub.2CH(SCH.sub.3)(CH.sub.2).sub.3                                                          t-C.sub.4 H.sub.9                                                                           120-121                       Ib-61                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        CH(OCH.sub.3)(CH.sub.2).sub.4                                                                  i-C.sub.3 H.sub.7                                                                           Oil                           Ib-62                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        CH(OCH.sub.3)(CH.sub.2).sub.4                                                                  t-C.sub.4 H.sub.9                                                                           Oil                           Ib-63                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(CO.sub.2 C.sub.2 H.sub.5)(CH.sub.2).su                     b.2              t-C.sub.4 H.sub.9                                                                           Oil                            ##STR417##                                                                    ##STR418##                                                                   __________________________________________________________________________

3.16 g (10 mmol) of the compound Ia-4 are introduced into 40 ml ofabsolute methylene chloride, 1.42 g (14 mmol) of triethylamine and aspatula-tip of DMAP is added, a solution of 1.38 g (13 mmol) of butyrylchloride in 20 ml of methylene chloride is added dropwise, and themixture is stirred for 16 hours at room temperature.

For working-up, the reaction mixture is washed using aqueous citricacid, NaHCO₃ solution and NaCl solution, dried and evaporated in arotary evaporator. Separation into the isomers is carried out by flashchromatography on silica gel using cyclohexane/ethyl acetate 6:1.

Yield: 0.92 g (24% of theory) of the unpolar trans isomer of m.p.85°-87° C. and 0.21 g (5% of theory) of the polar cis isomer of m.p.125°-126° C.

EXAMPLE Ic-1 ##STR419##

3.25 g (10 mmol) of the compound Ia-1 are introduced into 40 ml ofabsolute methylene chloride, 1.42 g (14 mmol) of triethylamine and aspatula-tip of DMAP are added, a solution of 1.47 g (12 mmol) ofisopropyl chloroformate in 20 ml of methylene chloride is addeddropwise, and the mixture is stirred for 16 hours at room temperature.

For working-up, the reaction mixture is washed using aqueous citricacid, NaHCO₃ solution and NaCl solution, dried and evaporated in arotary evaporator. Further purification is carried out byrecrystallization from MTB ether/n-hexane.

Yield: 2.84 g (69% of theory) of a solid of m.p. 136° C.

The compounds listed in Table 7 were prepared analogously:

                                      TABLE 7                                     __________________________________________________________________________     ##STR420##                                                                   Ex.                                                                           No.                                                                              X  Y   Z.sub.n                                                                           A    B           L M R.sup.2     m.p. °C.                __________________________________________________________________________    Ic-2                                                                             Cl Cl  H   (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  O O                                            i-C.sub.3 H.sub.7                              100                            Ic-3                                                                             CH.sub.3                                                                         CH.sub.3                                                                          H   (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  O O i-C.sub.3 H.sub.7                                                                         Oil                            Ic-4                                                                             CH.sub.3                                                                         CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  O O CH.sub.3    Oil                            Ic-5                                                                             CH.sub.3                                                                         CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  O O                                            i-C.sub.3 H.sub.7                                                                Oil                                                                        Ic-6                                                                             CH.sub.3                                                                         CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  O O                                            i-C.sub.4 H.sub.9                                                                Oil                                                                        Ic-7                                                                             CH.sub.3                                                                         CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.3).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  O O                                            s-C.sub.4 H.sub.9                                                                Oil                                                                        Ic-8                                                                             CH.sub.3                                                                         CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  O O C.sub.2 H.sub.5                                                                           Oil                            Ic-9                                                                             CH.sub.3                                                                         CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  O O                                            t-C.sub.4 H.sub.9                                                                120-130                                                                    Ic-10                                                                            CH.sub.3                                                                         CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.2)CH(OCH.sub.3)(CH.sub.2).sub.2                                                        O O C.sub.6 H.sub.5                                                                           Oil                            Ic-11                                                                            CH.sub.3                                                                         CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  O O                                                                                ##STR421## Oil                            Ic-12                                                                            CH.sub.3                                                                         CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  O O                                                                                ##STR422## Oil                            Ic-13                                                                            CH.sub.3                                                                         CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  O S                                            i-C.sub.3 H.sub.7                                                                131-140                                                                    Ic-14                                                                            CH.sub.3                                                                         CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR423##      O O                                            i-C.sub.3 H.sub.7                                                                87-89                                                                      Ic-15                                                                            CH.sub.3                                                                         CH.sub.3                                                                          H                                                                                  ##STR424##      O O                                            i-C.sub.3 H.sub.7                                                                84                                                                         Ic-16                                                                            CH.sub.3                                                                         CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR425##      O O                                            i-C.sub.3 H.sub.7                                                                73                                                                         Ic-17                                                                            CH.sub.3                                                                         CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR426##      O O                                            i-C.sub.4 H.sub.9                                                                Oil                                                                        Ic-18                                                                            CH.sub.3                                                                         CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                           O O C.sub.2 H.sub.5                                                                           Oil                            Ic-19                                                                            CH.sub.3                                                                         CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                           O O i-C.sub.3 H.sub.7                                                                         Oil                            Ic-20                                                                            Cl Cl  H   (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                           O O i-C.sub.3 H.sub.7                                                                         Oil                            Ic-21                                                                            CH.sub.3                                                                         CH.sub.3                                                                          H   (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                           O O i-C.sub.3 H.sub.7                                                                         Oil                            Ic-22                                                                            CH.sub.3                                                                         CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OC.sub.4 H.sub.9)(CH.sub.2).sub.2                                           O O i-C.sub.3 H.sub.7                                                                         Oil                            Ic-23                                                                            CH.sub.3                                                                         t-C.sub.4 H.sub.9                                                                 H   (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  O O i-C.sub.3 H.sub.7                                                                         Oil                            Ic-24                                                                            CH.sub.3                                                                         CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  O S t-C.sub.4 H.sub.9                                                                         Oil                            Ic-25                                                                            CH.sub.3                                                                         CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR427##      O O C.sub.2 H.sub.5                                                                           Oil                            Ic-26                                                                            CH.sub.3                                                                         CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR428##      O O i-C.sub.3 H.sub.7                                                                         Oil                            Ic-27                                                                            Cl Cl  H                                                                                  ##STR429##      O O i-C.sub.3 H.sub.7                                                                         106-108                        Ic-28                                                                            CH.sub.3                                                                         CH.sub.3                                                                          H                                                                                  ##STR430##      O O i-C.sub.3 H.sub.7                                                                         134-136                        Ic-29                                                                            CH.sub.3                                                                         CH.sub.3                                                                          6-CH.sub.3                                                                        CH.sub.2CH(SCH.sub.3)(CH.sub.2).sub.3                                                          O O C.sub.2 H.sub.5                                                                           99-101                         Ic-30                                                                            CH.sub.3                                                                         CH.sub.3                                                                          6-CH.sub.3                                                                        CH.sub.2 CH(SCH.sub.3)(CH.sub.2).sub.3                                                         O O i-C.sub.3 H.sub.7                                                                         128-129                        Ic-31                                                                            CH.sub.3                                                                         CH.sub.3                                                                          6-CH.sub.3                                                                        CH(OCH.sub.3)(CH.sub.2).sub.4                                                                  O O C.sub.2 H.sub.5                                                                           Oil                            Ic-32                                                                            CH.sub.3                                                                         CH.sub.3                                                                          6-CH.sub.3                                                                        CH(OCH.sub.3)(CH.sub.2).sub.4                                                                  O O i-C.sub.3 H.sub.7                                                                         111-112                        Ic-33                                                                            CH.sub.3                                                                         CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(CO.sub.2 C.sub.2 H.sub.5)(CH.sub.2).sub.2                                   O O i-C.sub.3 H.sub.7                                                                         Oil                            __________________________________________________________________________

EXAMPLE ld-1 ##STR431##

To 3.16 g (10 mmol) of enole Ia-4 in 40 ml of absolute CH₂ Cl₂ are firstadded 1.52 g (15 mmol) of triethylamine and then at 0°-10° C. a solutionof 1.48 g (13 mmol) CH₃ SO₂ Cl in 10 ml CH₂ Cl₂ are added dropwise.

The mixture is stirred for 2 hours at room temperature, then washed withaqueous citric acid (10%) and NaHCO₃ -solution, dried and evaporated.

The crude product is then mixed with 20 ml of petrol ether, suctionfiltered and dried.

Yield: 2.40 g of a solid (61% of theory), m.p. 130°-155° C.

The compounds listed in Table 8 were prepared analogously.

                                      TABLE 8                                     __________________________________________________________________________     ##STR432##                                                                   Ex. No.                                                                           X  Y  Z.sub.n                                                                           A    B          R.sup.3   m.p. °C.                       __________________________________________________________________________    Id-2                                                                              CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  ##STR433##                                                                             115-132                               __________________________________________________________________________

EXAMPLE Ie-1 ##STR434##

To a solution of 2.2 g of example No. Ia-4 in 10 ml of tetrahydrofuranare added 1.1 ml of triethylamine and then 1.42 g (0.007 mol) ofethanethiophosphonic acid propylthioether. The mixture is stirred for 3hours at 50° C., evaporated and the residue is chromatographed oversilica gel using hexane/ethyl acetate/acetone 30/10/1 as eluent. 2.1 g(62% of theory) of the compound shown are obtained as viscous oil(mixture of isomers).

¹ H-NMR (300 MHz, CDCl₃): δ=2.19, 2.20, 2.25, 2.26, (4S, 9H,Phenyl-CH₃), 3.15-3.25, 3.57 (2m, 1H, CH-OCH₃), 3.33, 3.39 (2s, 3H,OCH₃), 6.87 (s, 2H, phenyl-H)ppm

³¹ P-NMR(162 MHz, CDCl₃): δ=119.05, 119.64 ppm.

The compounds listed in Table 9 are prepared analogously.

                                      TABLE 9                                     __________________________________________________________________________     ##STR435##                                                                   Ex.                                      NMR                                  No.                                                                              X  Y  Z.sub.n                                                                           A    B          L R.sup.4                                                                          R.sup.5                                                                              δ (ppm)                        __________________________________________________________________________    Ie-2                                                                             CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                 S C.sub.2 H.sub.5                                                                  s-C.sub.4 H.sub.9S                                                                   3.39(s, 3H,                          cis                                      OCH.sub.3), 3.15-                                                             3.2(m, 1H                                                                     CHOCH.sub.3)                         Ie-2                                                                             CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                 S C.sub.2 H.sub.5                                                                  s-C.sub.4 H.sub.9S                                                                   3.32(s, 3H,                          trans                                    OCH.sub.3), 3.57                                                              (m, 1H, CH                                                                    OCH.sub.3)                           Ie-3                                                                             CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                 S CH.sub.3                                                                         H.sub.7 C.sub.3S                                                                     3.9(s, 3H,                           cis                                      OCH.sub.3)3.18-                                                               3.23(m, 1H,                                                                   CHOCH.sub.3)                         Ie-3                                                                             CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                 S CH.sub.3                                                                         H.sub.7 C.sub.3S                                                                     3.33(s, 3H,                          trans                                    OCH.sub.3), 3.57                                                              (m, 1H,                                                                       CHOCH.sub.3), 6.87,                                                           6.89(s, 2H,                                                                   ArH)                                 __________________________________________________________________________

EXAMPLE II-1 ##STR436## EXAMPLE II -2

18.40 g (0.10 mol) of ethyl 2-hydroxy-norbornane-2-carboxylate and 24.59g (0.11 mol) of 2,4-dichlorophenylacetyl chloride are refluxed for 16hours in 100 ml of absolute toluene and the mixture is evaporated in arotary evaporator. The compound shown above is obtained in a yield of37.10 g (quantitatively) in the form of an oil.

The compounds listed in Table 10 were prepared analogously.

                                      TABLE 10                                    __________________________________________________________________________     ##STR437##                                                                   Ex.                                                                           No.                                                                              X  Y   Z.sub.n                                                                           A    B           R.sup.8                                                                          m.p. °C.                             __________________________________________________________________________    II-2                                                                             Cl Cl  H   (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  C.sub.2 H.sub.5                                                                  Oil                                         II-3                                                                             CH.sub.3                                                                         CH.sub.3                                                                          H   (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  C.sub.2 H.sub.5                                                                  Oil                                         II-4                                                                             CH.sub.3                                                                         CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.2)(CH.sub.2).sub.2                                                  C.sub.2 H.sub.5                                                                  Oil                                         II-5                                                                             CH.sub.3                                                                         CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR438##      C.sub.2 H.sub.5                                                                  Oil                                         II-6                                                                             CH.sub.3                                                                         CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR439##      C.sub.2 H.sub.5                                                                  Oil                                         II-7                                                                             CH.sub.3                                                                         CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR440##      C.sub.2 H.sub.5                                                                  Oil                                         II-8                                                                             CH.sub.3                                                                         CH.sub.3                                                                          H                                                                                  ##STR441##      C.sub.2 H.sub.5                                                                  Oil                                         II-9                                                                             CH.sub.3                                                                         CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR442##      C.sub.2 H.sub.5                                                                  Oil                                         II-10                                                                            CH.sub.3                                                                         CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                           C.sub.2 H.sub.5                                                                  Oil                                         II-11                                                                            Cl Cl  H   (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                           C.sub.2 H.sub.5                                                                  Oil                                         II-12                                                                            CH.sub.3                                                                         CH.sub.3                                                                          H   (CH.sub.2).sub.2CH(OC.sub.2 H.sub.5)(CH.sub.2).sub.2                                           C.sub.2 H.sub.5                                                                  Oil                                         II-13                                                                            CH.sub.3                                                                         CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.2).sub.2(CH(O-n-C.sub.3 H.sub.7)(CH.sub.2).sub.2                                       C.sub.2 H.sub.5                                                                  Oil                                         II-14                                                                            CH.sub.3                                                                         CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(O-n-C.sub.4 H.sub.9)(CH.sub.2).sub.2                                        C.sub.2 H.sub.5                                                                  Oil                                         II-15                                                                            CH.sub.3                                                                         t-C.sub.4 H.sub.9                                                                 H   (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  C.sub.2 H.sub.5                                                                  Oil                                         II-16                                                                            CH.sub.3                                                                         t-C.sub.4 H.sub.9                                                                 6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(OCH.sub.3)(CH.sub.2).sub.2                                                  C.sub.2 H.sub.5                                                                  Oil                                         II-17                                                                            CH.sub.3                                                                         CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR443##      C.sub.2 H.sub.5                                                                  Oil                                         II-18                                                                            Cl Cl  H                                                                                  ##STR444##      C.sub.2 H.sub.5                                                                  Oil                                         II-19                                                                            CH.sub.3                                                                         CH.sub.3                                                                          H                                                                                  ##STR445##      C.sub.2 H.sub.5                                                                  Oil                                         II-20                                                                            CH.sub.3                                                                         CH.sub.3                                                                          6-CH.sub.3                                                                        CH.sub.2CH.sub.2 (SCH.sub.3)(CH.sub.2).sub.3                                                   C.sub.2 H.sub.5                                                                  Oil                                         II-21                                                                            CH.sub.3                                                                         CH.sub.3                                                                          6-CH.sub.3                                                                        CH(OCH.sub.3)(CH.sub.2).sub.4                                                                  C.sub.2 H.sub.5                                                                  Oil                                         II-22                                                                            CH.sub.3                                                                         CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(CO.sub.2 C.sub.2 H.sub.5)(CH.sub.2).sub.2                                   C.sub.2 H.sub.5                                                                  Oil                                         II-23                                                                            CH.sub.3                                                                         CH.sub.3                                                                          6-CH.sub.3                                                                        (CH.sub.2).sub.2CH(CO.sub.2 H)(CH.sub.2).sub.2                                                 C.sub.2 H.sub.5                                                                  Oil                                         __________________________________________________________________________

We claim:
 1. A compound of the formula ##STR446## in which A and Btogether with the carbon atom to which they are bonded form a cyclewhich is substituted by alkoxy, alkylthio, alkylsulphoxyl,alkylsulphonyl, carboxyl or CO₂ R² orA and B together with the carbonatom to which they are bonded represent a cycle in which twosubstituents together with the carbon atoms to which they are bondedrepresent a saturated cycle which is optionally substituted by alkyl,alkoxy or halogen and which can be interrupted by oxygen or sulphur, Xrepresents alkyl, halogen, alkoxy or halogenoalkyl, Y representshydrogen, alkyl, halogen, alkoxy or halogenoalkyl, Z represents alkyl,halogen or alkoxy, n represents a number from 0-3, or in which theradicals X and Z together with the phenyl radical to which they arebonded form the naphthalene radical of the formula ##STR447## in which Yhas the abovementioned meaning, and R⁸ represents alkyl.
 2. A compoundaccording to claim 1, in whichA and B together with the carbon atom towhich they are bonded form a saturated or unsaturated 3- to 8-memberedring which is substituted by C₁ -C₆ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄-alkylsulphoxyl or C₁ -C₄ -alkylsulphonyl, carboxyl or CO₂ R² or A and Btogether with the carbon atom to which they are bonded represent a C₃-C₈ -membered ring in which two substituents together with the carbonatoms to which they are bonded represent a saturated C₅ -C₇ -ring whichis optionally substituted by C₁ -C₆ -alkyl, C₁ -C₅ -alkoxy or halogenand which can be interrupted by oxygen or sulphur, X represents C₁ -C₆-alkyl, halogen, C₁ -C₆ -alkoxy or C₁ -C₃ -halogenoalkyl, Y representshydrogen, C₁ -C₆ -alkyl, halogen, C₁ -C₆ -alkoxy or C₁ -C₃-halogenoalkyl, Z represents C₁ -C₆ -alkyl, halogen or C₁ -C₆ -alkoxy, nrepresents a number from 0 to 3, or in which the radicals X and Ztogether with the phenyl radical to which they are bonded form thenaphthalene radical of the formula ##STR448## in which Y has the abovementioned meaning.
 3. A compound according to claim 1, in whichA and Btogether with the carbon atom to which they are bonded from a saturatedor unsaturated, 5- to 7-membered ring which is substituted by C₁ -C₅-alkoxy, C₁ -C₃ -alkylthio, C₁ -C₃ -alkylsulphoxyl, C₁ -C₃-alkylsulphonyl, carboxyl or CO₂ R² or A and B together with the carbonatom to which they are bonded represent a C₄ -C₇ -membered ring in whichtwo substituents together with the carbon atoms to which they are bondedrepresent a saturated C₅ -C₆ -ring which is optionally substituted by C₁-C₃ -alkyl, C₁ -C₃ -alkoxy, fluorine or chlorine and which can beinterrupted by oxygen or sulphur, X represents C₁ -C₆ -alkyl, halogen,C₁ -C₆ -alkoxy or C₁ -C₂ -halogenoalkyl, Y represents hydrogen, C₁ -C₆-alkyl, halogen, C₁ -C₆ -alkoxy or C₁ -C₂ -halogenoalkyl, Z representsC₁ -C₄ -alkyl, halogen or C₁ -C₄ -alkoxy, n represents a number from 0to 2, or in which the radicals X and Z together with the phenyl radicalto which they are bonded form the naphthalene radical of the formula##STR449## in which Y has the abovementioned meaning.
 4. A compoundaccording to claim 1, in whichA and B together with the carbon atom towhich they are bonded from a saturated or unsaturated 5- to 6-memberedring which is substituted by C₁ -C₄ -alkoxy, C₁ -C₂ -alkylthio, C₁ -C₂-alkylsulphoxyl, C₁ -C₂ -alkylsulphonyl, carboxyl or CO₂ R² or A and Btogether with the carbon atom to which they are bonded represent a C₄-C₆ -membered ring in which two substituents together with the carbonatoms to which they are bonded represent a saturated C₅ -C₆ -ring whichis optionally substituted by methyl, ethyl, methoxy, ethoxy, fluorine orchlorine and which can be interrupted by oxygen or sulphur, X representsmethyl, ethyl, propyl, i-propyl, fluorine, chlorine, bromine, methoxy,ethoxy or trifluoromethyl, Y represents hydrogen, methyl, ethyl, propyl,i-propyl, butyl, i-butyl, tert-butyl, fluorine, chlorine, bromine,methoxy, ethoxy or trifluoromethyl, Z represents methyl, ethyl,i-propyl, butyl, i-butyl, tert-butyl, fluorine, chlorine, bromine,methoxy or ethoxy, n represents 0 or
 1. 5. A process for the preparationof an O-aryl-α-hydroxy carboxylic ester according to claim 1 whichcomprisesa) acylating a 2-hydroxy carboxylic acid or ester of theformula ##STR450## in which R¹² represents hydrogen or alkyl and A and Bare defined in claim 1,with a phenylacetyl halide of the formula##STR451## in which X, Y, Z and n are defined in claim 1 and Halrepresents chlorine or bromine, optionally followed by esterification,or(b) esterifying a hydroxy carboxylic acid of the formula ##STR452## inwhich A, B, X, Y, Z, and n are defined in claim 1.